Tetrahydrofuran → Methyl 2-chloro-6-methylbenzoate

A solution of compound 1 (10.05 g, 64.04 mmol, 1.0 eq.) in THF (30 ml) was added dropwise to a suspension NaH (1.84 g, 76.85 mmol, 1.2 eq.) in THF (90 ml) at 0° C. and the mixture was stirred at same temperature for 1 h. Triethyl phosphonoacetate (16.5 ml, 83.25 mmol, 1.3 eq.) was added to the reaction mixture at −20° C. and the reaction mixture was allowed to warm to RT and stir for 2 h. The reaction mixture was diluted with ethyl acetate (100 ml), washed with water (2×100 ml) and the organic layer dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain the crude product which was purified by column chromatography (silica gel; 5% ethyl acetate/hexanes) to yield compound 2. Yield: 94% (17.28 g, 60.2 mmol).

1. stirringstir for 2 h
2. washwashed with water (2×100 ml)
3. dry with materialthe organic layer dried over sodium sulfate
4. customThe solvent was evaporated under reduced pressure
5. customto obtain the crude product which
6. customwas purified by column chromatography (silica gel; 5% ethyl acetate/hexanes)

ORD-Eintrag

ord-f81f8bab91c144c29fa392104c981c4c

Quelldatensatz

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08455475B2