Comments (6)
14.09.22
- Added NaH (163.9 mg, 4.01 mmol, 3.23 equiv.) to a dry 50 mL flask under nitrogen
- Added KBS3-3 (401 mg, 1.27 mmol) by solution transfer (3 mL dry DMF + 15 mL dry THF)
- Allowed to stir for 15 minutes at rt. Reaction was grey.
- Added propargyl bromide (0.5 mL, 80% in toluene, 4.67 mmol, 3.6 equiv.) and left stirring from 5 pm. Reaction was pale yellow.
from usyd_phd_eln.
15.09.22
TLC'd reaction at 10 am. Looked much the same as yesterday.
Added more propargyl bromide (0.2 mL) at 11.30 am and TLC'd again at 3 pm against reference of double-substituted product.
LRMS indicated nothing was present in reaction mixture but SM (peak at 339 is [M+Na]+).
Decided to abandon reaction. Will quench and attempt to recover starting material.
Next attempt will follow original method more closely - add NaH portionwise (and use only 3 equiv.), allow 1-2 hrs reaction time and cool reaction to 0 C before adding propargyl bromide.
from usyd_phd_eln.
19.09.22
Once again didn't actually quench and recover starting material - left over the weekend instead in the vague hope something would happen, and was pleasantly surprised.
TLC indicated that some of the desired bis-product has been produced.
R = reference spot of the bis-product. Eluent = 20:80 ethyl acetate:hexanes.\
-
Slowly added 25 mL NH4Cl (sat.) and left stirring
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Diluted with 50 mL water extra
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Extracted with toluene (3 X 50 mL)
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Washed with water (5 X 100 mL)
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Washed with brine (125 mL)
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Dried over magnesium sulfate and concentrated
Empty vial:
LRMS
KBS17-7 cr.d.zip
KBS17-7 cr.pdf
Peaks indicate SM (339.23, [M+Na]+), mono product (377.25, [M+Na]+ and desired bis product (415.26, [M+Na]+).
H NMR
Also indicates presence of both products.
KBS17-7 cr_1.zip
KBS17-7 cr processed.pdf
from usyd_phd_eln.
17.10.22
Columned crude product manually with ~ 11 cm silica, ~2cm diameter column.
Loaded slurry with pet. benz. and ran in ethyl acetate:pet. benz (given as % ethyl acetate).
5% - 100 mL
10% - 100 mL
20% - 200 mL
30% - 100 mL
100% - 100 mL
All run in same solvent system, 20% ethyl acetate in pet. benz.
Code | Fractions | Tare weight | Final weight | Mass | Percentage yield (see notes) |
---|---|---|---|---|---|
A | 10-14 | 15.9227 | 15.9379 | 15.2 | 3% |
B | 15-18 | 15.7223 | 15.7398 | 17.5 | 4% |
C | 19-20 | 15.6540 | 15.6670 | 12.7 | 3% |
D | 21-25 | 15.9306 | 16.0197 | 89.1 | 23% |
E | 26-31 | 15.7982 | 15.9069 | 108.7 | 24% |
F | >32 | 15.7357 | 15.8434 | 107.7 | 27% |
Total recovered yield: 84% by moles
For pure samples (B, D, F) - calculated moles according to m.w.
For mixed samples (C, E) - calculated moles according to m.w. of high m.w. component
from usyd_phd_eln.
H NMR
A
KBS17-7 A processed.pdf
Uploading KBS17-7 A_1.zip…
No clear product, just "junk".
B
KBS17-7 B processed.pdf
KBS17-7 B_1.zip
Appears to be desired product albeit in low concentration.
C - E
As expected - C = mixed mono/bis product, D = mono product, E = mixed mono product/SM
KBS17-7 C_1.zip
KBS17-7 D_1.zip
KBS17-7 E_1.zip
F
Perfect NMR spectrum of SM.
KBS17-7 F_1.zip
KBS17-7 F processed.pdf
from usyd_phd_eln.
LRMS
A
B
C
from usyd_phd_eln.
Related Issues (20)
- KBS43-1 - Nosyl protection of 1,6-diaminohexane HOT 7
- KBS29-6 - Bromination of KBS28 with phosphorus tribromide HOT 6
- KBS43 - master page HOT 2
- KBS43-2 - Nosyl protection of 1,6-diaminohexane HOT 4
- KBS44-1 - Nosyl deprotection of linear amines
- KBS23-6 - Azidation of 1-naphthylamine HOT 5
- KBS28-8 - Click coupling of 1-azidonaphthalene and propargyl alcohol HOT 4
- KBS29-7 - Bromination of KBS28 with phosphorus tribromide HOT 6
- KBS45-1 - Nosyl protection of 1,8-diaminooctane HOT 5
- KBS29 - master page HOT 3
- KBS30-4 - N-alkylation with KBS29 HOT 6
- KBS30 - master page HOT 5
- KBS45 - master page HOT 2
- KBS45-2 - Nosyl protection of 1,8-diaminooctane HOT 6
- KBS30-5 - N-alkylation with KBS29 HOT 7
- KBS28 - master page HOT 3
- KBS23 - master page HOT 4
- KBS46-1 - N-alkylation with KBS29 and KBS45 HOT 5
- KBS46 - master page HOT 1
- KBS48 - 49 (Mitsunobu reaction) - master page HOT 4
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