Iodoethylene → 1,1,1-Trifluoro-2-(2-mercapto-1,3-thiazol-5-yl)but-3-en-2-ol

Temperature

-78 °C

To a solution of vinyl iodide (1.88 g, 12.2 mmol) in Et2O at −78° C. was added t-butyl lithium (14.3 ml, 1.7 M/pentane, 24.3 mmol). The mixture was stirred at −78° C. for 1 h and warmed up to −30° C. for 5 min. The mixture was cooled back to −78° C. and 2,2,2-trifluoro-1-(2-mercapto-1,3-thiazol-5-yl)ethanone (1.18 g, 5.53 mmol) in Et2O was added. The reaction mixture stirred 30 min at −78° C., brought to 0° C. and partitioned between aqueous NH4Cl and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated and the residue chromatographed on silica gel (toluene/acetone; 90:10) to give the title compound.

1. temperaturewarmed up to −30° C. for 5 min
2. temperatureThe mixture was cooled back to −78° C.
3. stirringThe reaction mixture stirred 30 min at −78° C.
4. custombrought to 0° C.
5. custompartitioned between aqueous NH4Cl and EtOAc
6. customThe layers were separated
7. extractionthe aqueous phase was extracted with EtOAc
8. washThe combined organic layers were washed with brine
9. dry with materialdried over anhydrous Na2SO4
10. customThe solvent was evaporated
11. customthe residue chromatographed on silica gel (toluene/acetone; 90:10)

ORD record

ord-6688bbe9cb174e38b23a8b7707a6b987

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439260B2