Sodium Bicarbonate → 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzaldehyde

HRID 2387324Notes

Reaction equation

HRID 2387324 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([CH3:19])([CH3:18])[CH2:10][C@:11]1([C:14]([F:17])([F:16])[F:15])[CH2:13][O:12]1.C(=O)(O)[O-:21].[Na+]>CS(C)=O.[Cl-].[NH4+]>[CH3:18][C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH:2]=[O:21])([CH3:19])[CH2:10][C@:11]1([C:14]([F:17])([F:16])[F:15])[CH2:13][O:12]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 58026131(R)-2-[2-(2-bromomethylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Product 1

HCID 580261572-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzaldehydeYield 62%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of (R)-2-[2-(2-bromomethylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (46.6 g, 0.138 mol) in 300 mL of DMSO was added sodium bicarbonate (24 g, 0.285 mol) and the reaction mixture was heated to 70° C. After 24 hours, the reaction mixture was cooled to normal room temperature, diluted with 1200 mL of saturated aqueous ammonium chloride solution and extracted with four 250 mL portions of diethyl ether. The combined diethyl ether extracts were washed with brine, dried over anhydrous sodium sulfate, and the solvent evaporated in vacuo. The crude material was purified by column chromatography over silica gel (400 g) eluting with 0-15% ethyl acetate in hexanes and fractions corresponding to the major peak were pooled and solvent removed in vacuo to give 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzaldehyde as a light yellow oil (20 g, 62%).

Workup

  1. temperaturethe reaction mixture was cooled to normal room temperature
  2. extractionextracted with four 250 mL portions of diethyl ether
  3. washThe combined diethyl ether extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent evaporated in vacuo
  6. customThe crude material was purified by column chromatography over silica gel (400 g)
  7. washeluting with 0-15% ethyl acetate in hexanes and fractions corresponding to the major peak
  8. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-bf66b26bac9644249e89a0c64ff43ad8
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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