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

HRID 1620484ノート

反応式

HRID 1620484 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-56829e402d7247798566fb5f33dcdbac
出典データセット
uspto-grants-2014_07
特許番号
US08772277B2

反応ノート

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