Sodium Iodide → (S)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol

To a suspension of (S)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-((R)-toluene-4-sulfinylmethyl)pentan-2-ol (1.49 g, 3.23 mmol) and sodium iodide (1.45 g, 9.70 mmol) in 25 mL of anhydrous acetone at −40° C. was added a solution of trifluoroacetic acid anhydride (2.28 mL, 16.2 mmol) in 5 mL of anhydrous acetone via a syringe dropwise over 5 minutes. A greenish brown mixture was formed instantaneously. After 15 minutes, the reaction mixture was quenched with saturated aqueous sodium sulfite solution and neutralized with saturated aqueous sodium carbonate solution. The brown color disappeared and the crude was concentrated in vacuo to remove most of the acetone solvent. The resulting material was diluted with 50 mL of water and extracted with three 100 mL portions of ether. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford (S)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol as a yellow oil (1.43 g, 99%).

1. customA greenish brown mixture was formed instantaneously
2. customthe reaction mixture was quenched with saturated aqueous sodium sulfite solution
3. concentrationthe crude was concentrated in vacuo
4. customto remove most of the acetone solvent
5. additionThe resulting material was diluted with 50 mL of water
6. extractionextracted with three 100 mL portions of ether
7. washThe combined organic phases were washed with brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD 기록

ord-3d5cfdae34194a0babc69f2770548c39

출처 데이터셋

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07256300B2