Closed KlementineJBS closed 1 year ago
TLC indicated deprotonation step was not complete
Checked again after 2.5 hours. TLC indicated deprotonation was more progressed.
INSERT TLC
Empty vial: 15.6536 Full vial: 16.0547 Mass: 401.1
KBS17-9_1.zip KBS17-9 cr processed.pdf
Evidence of both mono and bis products.
KBS-17-9_1-D_5_1_392.d.zip KBS-17-9_1-D_5_1_392__Generic_Display_Report.pdf KBS-17-9_1-D_5_1_392_Compound_Spectrum_List_Report.pdf
10 cm silica
Ran ~ 200 mL of 5% ethyl acetate before disturbing column bed irreparably. Salvaged as much crude product as possible.
Salvaged product = 379.5 mg
Note that column numbering was continued across the two columns i.e. fraction 10 is the last collected before the column was ruined and fraction 11 is the first collected from the fresh column.
Second column
200 mL 5% ethyl acetate in petroleum benzine
250 mL 10%
200 mL 20%
50 mL 30%
200 mL 100%
Compound | Fractions | Tare weight | Final weight | Mass | Percentage yield (see notes) |
---|---|---|---|---|---|
Bis | 39-44 | 15.7929 | 15.8686 | 75.7 mg (0.192 mmol) | 15% |
Bis/mono | 45-46 | 15.7705 | 15.7783 | 17.8 mg (0.045 mmol) | 4% |
Mono | 47-51 | 15.7911 | 15.9331 | 142 mg (0.400 mmol) | 32% |
Mono/SM | 52-54 | 15.8134 | 15.8173 | 4 mg (0.00113 mmol) | < 1% |
SM | 55+ | 15.8383 | 15.9395 | 101.2 mg, 0.320 mmol) | 25% |
KBS17-9 F39-44_1.zip - bis product KBS17-9 45-46_1.zip - mixed bis/mono KBS17-9 F47-51_1.zip - mono product KBS17-9 55+_1.zip - starting material
KBS17-9 39-44.pdf Bis product - 415.26 [M+Na]+
KBS17-9 47-51.pdf Mono product - 377.23 [M+Na]+
KBS17-9 55+.pdf SM - 339.23 [M+Na]+
Decided to run 20% MeOH in DCM through column to get rid of last band - see image.
Link to HIRAC, original method and master page.
Last attempt is #33.
KBS17 Generic propargylation of 1,n-diamine.docx
Reaction Scheme
Changes to make