2-[4-(Trifluoromethyl)benzoyl]cyclopropanecarbonitrile → 2-{1-Hydroxy-1-[4-(trifluoromethyl)phenyl]ethyl}cyclopropanecarbonitrile

HRID 561456Notes

Reaction equation

HRID 561456 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]([F:20])([F:19])[C:6]1[CH:18]=[CH:17][C:9]([C:10]([CH:12]2[CH2:14][CH:13]2[C:15]#[N:16])=[O:11])=[CH:8][CH:7]=1>C(OCC)C>[OH:11][C:10]([CH:12]1[CH2:14][CH:13]1[C:15]#[N:16])([C:9]1[CH:17]=[CH:18][C:6]([C:5]([F:19])([F:20])[F:4])=[CH:7][CH:8]=1)[CH3:1]

Participants

4

Reactant 2

HCID 583920932-[4-(Trifluoromethyl)benzoyl]cyclopropanecarbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 583925112-{1-Hydroxy-1-[4-(trifluoromethyl)phenyl]ethyl}cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3.0 ml (9.09 mmol) of a 3N solution of methylmagnesium bromide in diethyl ether were added to 1.45 g (6.06 mmol) of the compound from Example 122A in 25 ml of diethyl ether at RT, and the mixture was stirred at RT overnight. The reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 1.40 g (90% of theory) of a mixture of the diastereomers of the title compound.

Workup

  1. additionThe reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)

Sources & evidence

ORD record
ord-1c2c57ba6943470a95f88ed490a8d2b3
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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