Aluminium lithium hydride → 3-(p-Chlorophenyl)-3-cyclopropyl-2-fluoro-2-propen-1-ol

HRID 1458391Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([CH:14]2[CH2:16][CH2:15]2)=[C:7]([F:13])[C:8](OCC)=[O:9])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:14]2[CH2:16][CH2:15]2)=[C:7]([F:13])[CH2:8][OH:9])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: -55 °C

Procedure

A solution of ethyl p-chloro-β-cyclopropyl-α-fluorocinnamate, (E)- and (Z)- (32.25 g, 0.12 mol) in ether is added dropwise to a mixture of lithium aluminum hydride (5.46 g, 0.144 mol) in ether while maintaining the temperature at -55° C. After the addition is complete, the reaction mixture is warmed to and stirred at -20° C. for 90 minutes, quenched sequentially with ethyl acetate, methanol and 2N hydrochloric acid, and extracted with ether. The organic extracts are combined, washed sequentially with water, saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a colorless oil (26.4 g, 97%).

Workup

additionAfter the addition
temperaturethe reaction mixture is warmed to and
customquenched sequentially with ethyl acetate, methanol and 2N hydrochloric acid
extractionextracted with ether
washwashed sequentially with water, saturated sodium hydrogen carbonate solution and water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a37ebb26591b47f4b026ffbc61818118
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849958

Reaction notes

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