Water → HCID 19599965, compound

HRID 611425Notes

Reaction equation

HRID 611425 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][O:7][C:6]=1[CH2:10][C:11](OC)=[O:12])=[O:4].[BH4-].[Na+].O>CO>[OH:12][CH2:11][CH2:10][C:6]1[O:7][CH:8]=[CH:9][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4208002HCID 4208002, compoundHCID 4311764Sodium borohydride

Product 1

HCID 19599965HCID 19599965, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.287 g (6.494 mmol) of methyl 3-methoxycarbonylfuran-2-ylacetate in 50 ml of methanol, 1.23 g (32.5 mmol) of sodium borohydride was added at room temperature, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into water and extracted with diethyl ether 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to yield the desired product.

Workup

  1. extractionextracted with diethyl ether 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-768c6886204c48529699ae18f3d8c2e3
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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