Ethyl Acetate → HCID 54189132, compound

HRID 987265Notes

Reaction equation

HRID 987265 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:7]=1[N+:20]([O-:22])=[O:21].[BH4-].[Na+].C(OCC)(=O)C>CO.CCCCCCC>[CH3:1][O:2][C:3](=[O:24])[CH:4]([OH:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:7]=1[N+:20]([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 8857Ethyl Acetate2×HCID 4311764Sodium borohydride2×HCID 541122243-(4-Benzyloxy-2-nitrophenyl)-2-oxopropanoic acid methyl ester

Product 1

HCID 54189132HCID 54189132, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8900HeptaneSolvent2×

Procedure

3-(4-Benzyloxy-2-nitrophenyl)-2-oxopropanoic acid methyl ester (4.1 g; 12.4 mmole) was dissolved in methanol (60 ml). Sodium borohydride (0.5 g; 13.12 mmole) was added in portions under stirring. TLC (silica gel, ethyl acetate:heptane, 1:1) after one hour showed remaining starting material and the formation of a by product. The reaction mixture was then cooled in an ice-bath and more sodium borohydride (0.2 g; 5.26 mmole) was added. After addition, the mixture was stirred at 0° C. until the starting material was consumed. The reaction mixture was evaporated to dryness. Ethyl acetate and water were added to the residue and the phases were separated. The organic phase was washed with brine and dried with magnesium sulfate and evaporated. Chromatography of the crude product on silica gel using a gradient of ethyl acetate in heptane as eluant gave 2.5 g (61% yield) of 3-(4-benzyloxy-2-nitrophenyl)-2-hydroxypropanoic acid methyl ester as an oil product.

Workup

  1. temperatureThe reaction mixture was then cooled in an ice-bath
  2. additionAfter addition
  3. stirringthe mixture was stirred at 0° C. until the starting material
  4. customwas consumed
  5. customThe reaction mixture was evaporated to dryness
  6. additionEthyl acetate and water were added to the residue
  7. customthe phases were separated
  8. washThe organic phase was washed with brine
  9. dry with materialdried with magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-489326d6b7ad4fb89c8c177c08dc5b7b
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

Loading…