Water → 2-[[(1S)-2-Azido-1-phenylethyl]oxy]-4-chloro-5-fluorobenzonitrile

HRID 1354391ノート

反応式

HRID 1354391 の反応式
[N:1]([CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6])=[N+:2]=[N-:3].[Cl:13][C:14]1[C:21]([F:22])=[CH:20][C:17]([C:18]#[N:19])=[C:16](F)[CH:15]=1.[H-].[Na+].O>CN(C=O)C>[N:1]([CH2:4][C@@H:5]([O:6][C:16]1[CH:15]=[C:14]([Cl:13])[C:21]([F:22])=[CH:20][C:17]=1[C:18]#[N:19])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 147803(S)-2-Azido-1-phenylethanolHCID 112753024-Chloro-2,5-difluorobenzonitrile

生成物 1

HCID 865989742-[[(1S)-2-Azido-1-phenylethyl]oxy]-4-chloro-5-fluorobenzonitrile収率 69.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The product from step (a) (1.75 g) and 4-chloro-2,5-difluorobenzonitrile (1.86 g) in dry DMF (40 ml) were treated with 60% sodium hydride in mineral oil (470 mg) with stirring under nitrogen. The reaction mixture was stirred for 2.5 h, poured into water, and extracted with ethyl acetate. The extract was washed with water (5×) then brine and dried (MgSO4). The solvent was evaporated and the residue purified by chromatography (silica, 10% ether/isohexane as eluent) to give the sub-title compound (2.37 g) as a pale yellow oil.

後処理

  1. stirringThe reaction mixture was stirred for 2.5 h
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water (5×)
  4. dry with materialbrine and dried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue purified by chromatography (silica, 10% ether/isohexane as eluent)

出典と根拠

ORDレコード
ord-51da321b998d407abd2db97bdb6c1796
出典データセット
uspto-grants-2007_05
特許番号
US07223794B2

反応ノート

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