Diethyl Ether → (4-Chlorophenyl)(2,2-difluorocyclopropyl)methanol

HRID 561483Notes

Reaction equation

HRID 561483 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH:12]2[CH2:14][C:13]2([F:16])[F:15])=[O:11])=[CH:6][CH:5]=1.[Cl-].[NH4+].C(OCC)C>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH:12]2[CH2:14][C:13]2([F:15])[F:16])[OH:11])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 248658712,2-Difluorocyclopropyl(4-chlorophenyl) ketone

Product 1

HCID 58392413(4-Chlorophenyl)(2,2-difluorocyclopropyl)methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

336 mg (8.89 mmol) of sodium borohydride were added to 1.75 g (8.08 mmol) of the compound from Example 124A in 33 ml of ethanol and 9 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 1 h. The reaction mixture was added to saturated aqueous ammonium chloride solution and diethyl ether, the phases were separated, the aqueous phase was extracted twice with diethyl ether, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. 1.44 g (82% of theory) of a mixture of the diastereomers of the title compound were obtained.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with diethyl ether
  3. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. addition1.44 g (82% of theory) of a mixture of the diastereomers of the title compound
  8. customwere obtained

Sources & evidence

ORD record
ord-fc5f375805a94fe8af6a928964fd7edd
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…