Trifluoroacetic acid → HCID 178442228, compound

Temperature

0 °C

To a solution of 3-(2-mercapto-1,3-thiazol-5-yl)pentan-3-ol (515 mg, 2.5 mmol) in 30 ml of CH2Cl2 at 0° C. was added triethylsilane (2.0 ml, 12.5 mmol) and TFA (2.0 ml, 25.9 mmol). The mixture was stirred for 1 h at 0° C. then warmed to room temperature. After 1 h, the reaction mixture was diluted with EtOAc and quenched with a saturated solution of sodium bicarbonate. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4 and the solvent evaporated. The crude compound showed a mixture of alkene and desired product. The crude mixture was then resubmitted to the same reaction condition to get complete conversion. The crude was chromatographed on silica gel (hexane:EtOAc; 95:5 to 80:20) to the title compound.

1. temperaturethen warmed to room temperature
2. waitAfter 1 h
3. customquenched with a saturated solution of sodium bicarbonate
4. customThe layers were separated
5. extractionthe aqueous phase was extracted with EtOAc
6. washThe combined organic layers were washed with brine
7. dry with materialdried over anhydrous MgSO4
8. customthe solvent evaporated
9. additiona mixture of alkene and desired product
10. customto get complete conversion
11. customThe crude was chromatographed on silica gel (hexane:EtOAc; 95:5 to 80:20) to the title compound

ORD record

ord-a61d031bfbbc43c7a8f3afbe68b62254

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439260B2