Triethylamine → HCID 13785433, compound

Isopropyl vinyl ketone (1.97 g, 20 mmol), prepared from isobutyryl chloride and vinyl trimethylsilane in accordance with the method detailed in Tet. Letters, (1979), 1995, was mixed with 4-fluorobenzaldehyde (2.4 g, 20 mmol), 2 ml (14 mmol) of triethylamine, and 1.0 g (4.0 mmol) of 2-(2-hydroxyethyl)-3-methyl-4-benzylthiazolium chloride. The mixture was stirred and heated under nitrogen for five hours. After cooling to room temperature, the mixture was partitioned between ether (200 ml) and water (50 ml). The water layer was extracted with 200 ml of ether and the ether solutions were combined. The combined ether solution was washed successively with 50 ml of water, two 50-ml portions of 2M hydrochloric acid, and 50 ml of brine. The ether solution was dried over anhydrous magnesium sulfate. After removal of the ether, the remaining liquid was flash chromatographed on silica gel eluting with 20:1 (volume/volume) hexane-ethyl acetate. This procedure afforded 2.59 g of pure 1-(4-fluorophenyl)-5-methyl-1,4-hexanedione, mp 47°-49° C.

1. temperatureheated under nitrogen for five hours
2. customthe mixture was partitioned between ether (200 ml) and water (50 ml)
3. extractionThe water layer was extracted with 200 ml of ether
4. washThe combined ether solution was washed successively with 50 ml of water, two 50-ml portions of 2M hydrochloric acid, and 50 ml of brine
5. dry with materialThe ether solution was dried over anhydrous magnesium sulfate
6. customAfter removal of the ether
7. customchromatographed on silica gel eluting with 20:1 (volume/volume) hexane-ethyl acetate

ORD record

ord-a1dc963a71f04cf0ac97aabaca40b790

Source dataset

uspto-grants-1987_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04647576