Tetrabutylammonium Fluoride → HCID 66761841, compound

To a solution of (2E)-3-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-chlorophenyl]acrylonitrile from the previous step (1 eq.) in toluene (0.01 M) was added at 80° C. benzenesulfonyl hydrazide (3×1 eq.) over 3 h. The reaction mixture was diluted with EtOAc and washed sequentially with water, sat. aq. NaHCO3 and brine. Drying over MgSO4, filtration and concentration of the filtrate in vacuo afforded a yellow oil. The residue was taken up in THF (0.1 M) and added tetrabutylammonium fluoride (1.0 M THF solution, 1.1 eq.). The resulting reaction mixture was stirred at RT for 2 h. After quenching the reaction with sat. aq. NH4Cl, the mixture was extracted with EtOAc. The combined organic extracts were washed with sat. aq. NaHCO3 and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo and purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a pale yellow oil.

1. washwashed sequentially with water, sat. aq. NaHCO3 and brine
2. dry with materialDrying over MgSO4, filtration and concentration of the filtrate in vacuo
3. customafforded a yellow oil
4. customThe resulting reaction mixture
5. customAfter quenching
6. customthe reaction with sat. aq. NH4Cl
7. extractionthe mixture was extracted with EtOAc
8. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. customConcentration of the filtrate in vacuo and purification of the crude product
12. customthus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

ORD record

ord-0819716e2c0d482f80e8abc82408e138

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2