6-Oxabicyclo[3.1.0]hexane → (1S,2R)-2-(3,5-difluorophenyl)cyclopentanol

HRID 475801Notes

Reaction equation

HRID 475801 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH:11]12[O:16][CH:15]1[CH2:14][CH2:13][CH2:12]2>C1COCC1.[Cu]I>[F:1][C:2]1[CH:3]=[C:4]([C@H:14]2[CH2:13][CH2:12][CH2:11][C@@H:15]2[OH:16])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 178505930HCID 178505930, compound

Product 1

HCID 10976443(1S,2R)-2-(3,5-difluorophenyl)cyclopentanolYield 90%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with (3,5-difluorophenyl)magnesium bromide (149 mL, 149 mmol) and copper (I) iodide (1.901 g, 9.98 mmol). To this reaction mixture, 6-oxabicyclo[3.1.0]hexane (12.53 g, 149 mmol) dissolved in THF (25 mL) was added dropwise. The reaction mixture warmed upon the addition of the epoxide. The reaction was stirred at rt for 2 h at rt. The reaction mixture was quenched by the addition of a solution of ammonium chloride. Ether was added and the organic layer was collected, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to afford (1S,2R)-2-(3,5-difluorophenyl)cyclopentanol (26.5 g, 134 mmol, 90% yield).

Workup

  1. additionwas added dropwise
  2. customThe reaction mixture was quenched by the addition of a solution of ammonium chloride
  3. additionEther was added
  4. customthe organic layer was collected
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-21029c2a780c4d12842cf4b74e4bf334
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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