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

HRID 522672Notes

Reaction equation

HRID 522672 reaction equation
[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]

Participants

4

Reactant 2

HCID 522372Ethyl 4-nitrophenylglyoxylateHCID 4311764Sodium borohydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-0847ec92062c450c8e46aa7ba411e8fe
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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