Dimethyl Sulfoxide → 1-[2,4-Bis(trifluoromethyl)benzyl]-7-oxoazepane-4-carbaldehyde

HRID 1620635ノート

反応式

HRID 1620635 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]([F:35])([F:34])[C:13]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:14]=1[CH2:15][N:16]1[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18][C:17]1=[O:25].[Cl-].[NH4+]>ClCCl.C(N(CC)CC)C>[F:35][C:12]([F:11])([F:34])[C:13]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:14]=1[CH2:15][N:16]1[C:17](=[O:25])[CH2:18][CH2:19][CH:20]([CH:23]=[O:24])[CH2:21][CH2:22]1

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 866788011-[2,4-Bis(trifluoromethyl)benzyl]-5-(hydroxymethyl)azepan-2-one

生成物 1

HCID 866788021-[2,4-Bis(trifluoromethyl)benzyl]-7-oxoazepane-4-carbaldehyde収率 46.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒3 回HCID 8471Triethylamine溶媒

実験手順

To a solution of DMSO (1.40 g) in dichloromethane (100 mL) was slowly added a solution of oxalyl chloride (2.48 g) in dichloromethane (200 mL) at −78° C. The reaction mixture was stirred for 5 min, a solution of 1-[2,4-bis(trifluoromethyl)benzyl]-5-(hydroxymethyl)azepan-2-one (6.0 g) in dichloromethane (100 mL) was added dropwise, and the mixture was stirred for 15 min. Triethylamine (8.2 g) was added and the mixture was allowed to warm to room temperature. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (2.76 g).

後処理

  1. stirringthe mixture was stirred for 15 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-fe932f345f2d47a3bc7fd82c2e807935
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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