Hydrochloric Acid → HCID 12520963, compound

Temperature

0 °C

A heterogenous solution of acid-washed zinc powder (4.74 g, 72,5 mmol), 3-pentanone (3.84 ml, 36.4 mmol), and dry THF (25 ml) was cooled to 0° C. in an ice-water bath, and a mixture of 3-bromo-3,3-difluoropropene (6.00 g, 38.2 mmol) in dry THF (10 ml) was slowly added. The reaction mixture was allowed to stand at room temperature overnight. Then, aqueous hydrochloric acid (5%, 30 ml) was added to the reaction mixture, which was stirred for 5 minutes. Excess zinc was removed by filtration and washed with ether. The organic phase was washed with saturated sodium bicarbonate solution, water (twice), dried over MgSO4 and concentrated. This oil was dissolved in dichloromethane (50 ml), and triethylamine (7.05 ml, 50.8 mmol) and 4-(N,N-dimethylamino)-pyridine (250 mg) are added. The reaction mixture was cooled to 0° C. and trimethylsilyl chloride (6.42 ml, 50.8 mmol) was added dropwise, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water and extracted twice with ether. The combined organic layers were washed several times with water, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography (50 g silica gel; 2% EtOAc in petroleum ether as eluant) to give the compound as a colourless oil, δ 0.13 (s, 9H), 0.89 (m, 6H), 1.5-1.8 (m, 4H), 5.43 (m, 1H), 5.63 (m, 1H), 5.92-6.13 (m, 1H).

1. additionwas slowly added
2. customExcess zinc was removed by filtration
3. washwashed with ether
4. washThe organic phase was washed with saturated sodium bicarbonate solution, water (twice),
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. dissolutionThis oil was dissolved in dichloromethane (50 ml)
8. stirringthe mixture was stirred at room temperature overnight
9. extractionextracted twice with ether
10. washThe combined organic layers were washed several times with water
11. dry with materialdried over MgSO4
12. customevaporated in vacuo
13. customThe residue was purified by chromatography (50 g silica gel; 2% EtOAc in petroleum ether as eluant)

ORD record

ord-363aa985c38c4545abfbcf1f6ed6e9a2

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05710142