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

HRID 522672노트

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HRID 522672 반응식
[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]

참가 물질

4

반응물 2

HCID 522372Ethyl 4-nitrophenylglyoxylateHCID 4311764Sodium borohydride

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-0847ec92062c450c8e46aa7ba411e8fe
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334263B2

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