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110482-97-8

2,2-difluoropent-4-en-1-ol synthesis

3synthesis methods
-

Yield: 70%

Reaction Conditions:

in ethanol

Steps:

III 2,2-difluoro-4-pentene-1-ol (28)
2,2-difluoro-4-pentene-1-ol (28) A solution of 2,2-difluoro-4-pentenoic acid ethyl ester (32.5 g, 198 mmoles) in ethanol (100 ml) is added to a suspension of sodiumborohydride (5.7 g, 150 mmoles) in ethanol (100 ml), previously cooled to 0° C., at such a rate that the internal temperature is maintained below 10° C. The reaction mixture is kept at room temperature for 2 hours, hydrolyzed carefully with 1N H2 SO4 and water, and diluted with dichloromethane (600 ml). The organic layer is washed twice with brine (2*250 ml), dried over sodium sulfate, and concentrated under reduced pressure (500 mm Hg, 25° C.). Distillation of the residue (15 mm, 42°-46° C.) affords pure (28) (17.05 g, 70%).

References:

Merrell Dow Pharmaceuticals Inc. US4730006, 1988, A