Lithium borohydride → 2-Thiophenemethanol, 5-[4-(trifluoromethyl)phenyl]-

To a solution of 5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (3.02 g, 11.8 mmole) in THF (100 mL), is added to LiBH4 (1.75 g, 80.24 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 1 hour. The reaction is quenched using 5N HCl (100 mL) at 0° C. The THF is removed on rota vapor, the aqueous solution is then extracted with ethyl acetate (2×100 mL). The combined organic solution is washed with brine (3×200 mL), dried over Na2SO4 and concentrated. The crude product is purified on a silica gel column, eluting with 20% ethyl acetate in hexane and concentrated to provide the titled compound as off-white solid.

1. customThe reaction is quenched
2. customat 0° C
3. customThe THF is removed on rota vapor
4. extractionthe aqueous solution is then extracted with ethyl acetate (2×100 mL)
5. washThe combined organic solution is washed with brine (3×200 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe crude product is purified on a silica gel column
9. washeluting with 20% ethyl acetate in hexane
10. concentrationconcentrated

ORD-Eintrag

ord-d9b5e75adf0e48869f9a9fff941b564e

Quelldatensatz

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07504433B2