Sodium borohydride → Methyl 2-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409426ノート

反応式

HRID 1409426 の反応式
[CH:1]([C:3]1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:19])[CH3:18])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 58638526methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate

生成物 1

HCID 70980902Methyl 2-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

Into a flask containing a solution of methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate (3 g, 10.5 mmol) in MeOH (20 ml), NaBH4 (0.401 g, 10.5 mmol) was added in portions at 0° C. The resulting mixture was allowed to stir at 0° C. for 30 min followed by RT for 1 hour. The reaction mixture was concentrated and the crude was diluted with water and extracted with EtOAc. The organic layer was concentrated under reduced pressure. Yield 1.5 g. LC-MS: [M+1]=287.17.

後処理

  1. additionwas added in portions at 0° C
  2. waitfollowed by RT for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. additionthe crude was diluted with water
  5. extractionextracted with EtOAc
  6. concentrationThe organic layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-5343b9fe06724720a7c313978e2712a2
出典データセット
uspto-grants-2014_12
特許番号
US08921378B2

反応ノート

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