Water → 4-Hydroxymethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester

HRID 29328Notes

Reaction equation

HRID 29328 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:10]([CH3:11])=[C:9]2[C:12](=[C:16]=[O:17])[CH:13]=[CH:14][CH:15]=[C:8]2[O:7]1)=[O:5])[CH3:2].[BH4-].[Na+].O>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 865990284-Carbonyl-3-methylbenzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687118924-Hydroxymethyl-3-methylbenzofuran-2-carboxylic acid ethyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.123 g (0.530 mmol) of 4-carbonyl-3-methylbenzofuran-2-carboxylic acid ethyl ester in 10 mL of ethanol was added 0.019 g (0.505 mmol) of sodium borohydride. The reaction was stirred at room temperature for 2 h and than diluted wuth water and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to provide 0.113 g of 4-hydroxymethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-6cd94ab7971b402682225449c31167ce
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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