Ethyl 4-nitrophenylglyoxylate → 1-(4-nitrophenyl)ethane-1,2-diol

HRID 522672ノート

反応式

HRID 522672 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:16])[C:11](OCC)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:16])[CH2:11][OH:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

4

反応物 2

HCID 522372Ethyl 4-nitrophenylglyoxylateHCID 4311764Sodium borohydride

生成物 1

HCID 41172001-(4-nitrophenyl)ethane-1,2-diol収率 91.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of ethyl 2-(4-nitrophenyl)-2-oxoacetate (10.0 g, 47.8 mmol) in ethanol (100 mL) was slowly added sodium borohydride (4.54 g, 119.5 mmol) at 0° C. After the addition was completed, the reaction mixture was allowed to warm to RT and stirred for 12 h. The reaction was quenched by acetone (10 mL) and concentrated. The residue was purified by silica gel column chromatography (dichloromethane/methanol=5/1) to afford the title compound (8.0 g, 87%) as a brown solid. MS (ES+) C8H9NO4 requires: 183, found: 184 [M+H]+.

後処理

  1. customat 0° C
  2. additionAfter the addition
  3. customThe reaction was quenched by acetone (10 mL)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol=5/1)

出典と根拠

ORDレコード
ord-0847ec92062c450c8e46aa7ba411e8fe
出典データセット
uspto-grants-2016_05
特許番号
US09334263B2

反応ノート

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