Hydrochloric Acid → 2-Ethyl-3,3-bis(4-fluorophenyl)-2-propenol

HRID 1086093Notes

Reaction equation

HRID 1086093 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([C:13](=[C:19]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:14](OCC)=[O:15])[CH3:12].Cl>C(Cl)Cl>[CH2:11]([C:13](=[C:19]([C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[CH2:14][OH:15])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15133044Ethyl 2-ethyl-3,3-bis(4-fluorophenyl)propenoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 151330492-Ethyl-3,3-bis(4-fluorophenyl)-2-propenolYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisobutylaluminum hydride (79 mL of 1M solution, 79 mmol) was added to a solution of ethyl 2-ethyl-3,3-bis(4-fluorophenyl)propenoate (8.3 g, 26.3 mmol) in 150 mL of methylene chloride at -70° C. After stirring for 3 hours, the mixture was hydrolyzed by adding 2N hydrochloric acid. The aqueous fraction was separated and extracted with methylene chloride. The combined organic fractions were dried with magnesium sulfate and concentrated in vacuo to give 7 g of the title compound as an oil; MS(CI): m/e =274 for M+ of C17H16F2O.

Workup

  1. customThe aqueous fraction was separated
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic fractions were dried with magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2635df309ffe4e02b4d73c38d7c8431b
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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