Sodium borohydride → HCID 86592464, compound

HRID 1271258Notes

Reaction equation

HRID 1271258 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][O:5][CH2:6]/[CH:7]=[CH:8]/[CH:9]=[O:10].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:11])[CH2:4][O:5][CH2:6]/[CH:7]=[CH:8]/[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86592462HCID 86592462, compound

Product 1

HCID 86592464HCID 86592464, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 311 mg of 2-[3-formyl-(E)-2-propen-1-yloxy]acetic acid methyl ester in 10 ml of methanol, 149 mg of sodium borohydride was added, followed by stirring at room temperature for 4.5 hours. The solvent was evaporated under reduced pressure and the residue was extracted with ethyl acetate after adding ice water. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 187 mg of the desired crude product as an oily substance.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. additionafter adding ice water
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a68ad080653d42a6b80c3346c53959b7
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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