Triethylamine → 1-[2,4-Bis(trifluoromethyl)benzyl]azetidine-3-carbaldehyde

HRID 1620484Notes

Reaction equation

HRID 1620484 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:4]=1[CH2:5][N:6]1[CH2:9][CH:8]([CH2:10][OH:11])[CH2:7]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CS(C)=O>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:4]=1[CH2:5][N:6]1[CH2:7][CH:8]([CH:10]=[O:11])[CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86678675{1-[2,4-Bis(trifluoromethyl)benzyl]azetidin-3-yl}methanol

Product 1

HCID 866786761-[2,4-Bis(trifluoromethyl)benzyl]azetidine-3-carbaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of {1-[2,4-bis(trifluoromethyl)benzyl]azetidin-3-yl}methanol (313 mg) and triethylamine (607 mg) in DMSO (5 mL) was added sulfur trioxide pyridine complex (477 mg) at room temperature. The reaction mixture was stirred at room temperature overnight. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (202 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-56829e402d7247798566fb5f33dcdbac
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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