Methanol → HCID 592349, compound

HRID 2286803Notes

Reaction equation

HRID 2286803 reaction equation
[F:1][C:2](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](OCC)=[O:4].[H-].C([Al+]CC(C)C)C(C)C.CO.[H][H]>C1C=CC=CC=1>[F:1][C:2](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][OH:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 606552HCID 606552, compoundHCID 21225700Diisobutylaluminumhydride2×HCID 178418361HCID 178418361, compound

Product 1

HCID 592349HCID 592349, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of the above ester (1.80 g, 9.27 mmol) in 50 ml benzene is added dripwise at RT a 1.78 M solution of diisobutyl aluminum hydride; stir 20 minutes. Add 3 ml more diisobutyl aluminum hydride. Reaction is worked up by adding MeOH until hydrogen evolution ceases, then extracting in ether/dilute HCl solution. The aqueous layer is extracted 2X with ether. The ether layers are washed with dil. HCl, water and brine, dried (Na2SO4) and evaporated under vacuum to yield 2-fluoro-3-phenyl-2-propen-1-ol.

Workup

  1. customReaction
  2. extractionextracting in ether/dilute HCl solution
  3. extractionThe aqueous layer is extracted 2X with ether
  4. washThe ether layers are washed with dil. HCl, water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-397ac21d919b4aa2adb867c567a79156
Source dataset
uspto-grants-1981_05
Patent number
US04267359

Reaction notes

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