Methanol → HCID 592349, compound

HRID 1395614Notes

Reaction equation

HRID 1395614 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 2× 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 2× 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-10bad4cf46654b15a40e788f5c2cefb4
Source dataset
uspto-grants-1980_05
Patent number
US04204071

Reaction notes

Loading…