Hydrochloric Acid → 5-methoxy-1-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol

To a stirred solution of 5-methoxy-1-indanone (1.00 g, 6.17 mmol) and trifluoromethyltrimethylsilane (1.32 g, 9.26 mmol) in dry THF (15 ml) was added 1.0M THF solution of tetrabutylammonium fluoride (0.05 ml) with ice-cooling.The reaction mixture was stirred at room temperature for 21 h. To a mixture was 1N HCl (20 ml). and stirred at room temperature for 25 h. The reaction mixture was diluted with CH2Cl2-water. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with water and brine, dried (MgSO4) and concentrated in vacuo to give crude product as a dark yellow oil. The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate(5:1-3:1) to give Compound 62 (1.05 g, 73%) as a yellow oil.

1. customwith ice-cooling.The reaction mixture
2. stirringand stirred at room temperature for 25 h
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with CH2Cl2
5. washThe combined solution was washed with water and brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customto give crude product as a dark yellow oil
9. customThe crude product was purified by column chromatography on silica gel with hexane-ethyl acetate(5:1-3:1)

ORD record

ord-da738617294547719878d5fd96b6b3d4

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06329396B1