Sodium borohydride → 2-(5-Chloro-1,3-dihydro-2-benzofuran-1-yl)ethanol

Ethyl (5-chloro-1,3-dihydro-2-benzofuran-1-yl)-acetate (2.79 g, 11.6 mmol) in THF (60 mL) was cooled to −78° C. and di-isobutylaluminium hydride (1M in toluene) (12.7 mL, 12.7 mmol) was added dropwise. After 1 h, the reaction mixture was quenched with a saturated solution of sodium tartrate (150 mL), allowed to warm to room temperature and stirred for 1 h. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered and evaporated in vacuo. The resultant crude intermediate was dissolved in methanol (50 mL), cooled to 0° C., and sodium borohydride (0.48 g, 12.7 mmol) added in portions. The reaction was quenched with saturated sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by column chromatography, eluting with ethyl acetate/hexane (1:2), to yield the title compound as a white solid.

1. customthe reaction mixture was quenched with a saturated solution of sodium tartrate (150 mL)
2. customThe layers were separated
3. extractionthe aqueous layer extracted with ethyl acetate
4. dry with materialThe combined organic layers were dried (MgSO4)
5. filtrationfiltered
6. customevaporated in vacuo
7. dissolutionThe resultant crude intermediate was dissolved in methanol (50 mL)
8. temperaturecooled to 0° C.
9. customThe reaction was quenched with saturated sodium hydrogen carbonate
10. extractionextracted with ethyl acetate
11. washThe combined organic layers were washed with brine
12. dry with materialdried (MgSO4)
13. filtrationfiltered
14. customevaporated in vacuo
15. customThe crude product was purified by column chromatography
16. washeluting with ethyl acetate/hexane (1:2)

ORD record

ord-0bbe3e3bf7b848448115fcdc0ad9dab6

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07335660B2