Sodium borohydride → [5-(3-Chlorophenyl)isoxazol-3-yl]methanol

HRID 1453798ノート

反応式

HRID 1453798 の反応式
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[O:14][N:13]=[C:12]([C:15](OCC)=[O:16])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1>CO>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[O:14][N:13]=[C:12]([CH2:15][OH:16])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 46929188Ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylate

生成物 1

HCID 57528605[5-(3-Chlorophenyl)isoxazol-3-yl]methanol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

Sodium borohydride (96.7 g, 2.6 mol) was slowly added to a solution of ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylate (214.5 g, 0.85 mol) in methanol (2.5 L) at 0° C. The reaction mixture was heated at 50° C. for 2 h and was quenched with EtOAc at r.t. Most of the solvent was distilled off and to the remaining crude was added EtOAc. The organic layer was washed with water, saturated brine and concentrated to give the title compound, which was used directly in the next step. MS (M++1)=210.

後処理

  1. customwas quenched with EtOAc at r.t
  2. distillationMost of the solvent was distilled off and to the remaining crude
  3. additionwas added EtOAc
  4. washThe organic layer was washed with water, saturated brine
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-12c5278033dc4b20816c3773871ca6c2
出典データセット
uspto-grants-2009_01
特許番号
US07476684B2

反応ノート

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