Water → HCID 57602810, compound

Into a cooled (−10° C.) solution of 5.25 g (21.68 mmol) of 2-fluoro-2-phosphonoacetic acid triethyl ester in tetrahydrofuran (30 mL) under an atmosphere of argon was dropped 13.2 mL (19.87 mmol) of 1.5 mol/L n-butyllithium in hexane (available from KANTO KAGAKU). After stirring for 20 minutes at room temperature, 2.0 g (19.87 mmol) of tetrahydropyran-4-one was dropped thereto and stirred for 2 hours at about 55° C. The obtained mixture was left to cool to room temperature and then poured into water, followed by extraction with ether. The ether extract was washed with water (three times) and saturated brine and dried over anhydrous magnesium sulfate, and the solvent was removed. The obtained residue was purified by medium pressure liquid column chromatography on silica gel (developing solvent: hexane-ethyl acetate) to obtain 3.32 g (yield 88.8%) of fluoro-(tetrahydropyran-4-ylidene)acetic acid ethyl ester (IX-16) as colorless liquid. Its physical property is shown blow.

1. stirringstirred for 2 hours at about 55° C
2. waitThe obtained mixture was left
3. temperatureto cool to room temperature
4. extractionfollowed by extraction with ether
5. extractionThe ether extract
6. washwas washed with water (three times) and saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. customthe solvent was removed
9. customThe obtained residue was purified by medium pressure liquid column chromatography on silica gel (developing solvent: hexane-ethyl acetate)

ORD record

ord-f0c4cdd380964b5f8fd335b8114b5110

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07511144B2