Sodium borohydride → HCID 12496770, compound

HRID 29331Notes

Reaction equation

HRID 29331 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16]Br)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[BH4-].[Na+]>CS(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 687165554-Bromomethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 12496770HCID 12496770, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 0.291 g (0.98 mmol) of 4-bromomethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester in 5 mL of DMSO was added 0.074 g (1.96 mmol) of sodium borohydride and the reaction was stirred at room temperature for 2 h. The reaction was diluted with water and extracted with ether. The organics were washed with water and brine, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10) to provide 0.209 g of 4-methyl-3-methylbenzofuran-2-carboxylic acid ethyl ester.

Workup

  1. extractionextracted with ether
  2. washThe organics were washed with water and brine
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10)

Sources & evidence

ORD record
ord-6c075c0a962b4d4c8206d3b9c196aade
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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