Acetone → 5-[(6-Bromo-2-pyridyl)-methyl]-tetrahydrofuran-2-one

HRID 1756346Notes

Reaction equation

HRID 1756346 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6](=O)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[N:9]=1.[BH4-].[Na+].CC(C)=O>CO>[Br:14][C:10]1[N:9]=[C:8]([CH2:7][CH:6]2[O:16][C:3](=[O:2])[CH2:4][CH2:5]2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 156617995-(6-Bromo-2-pyridyl)-4-oxo-pentanoic acid methyl ester

Product 1

HCID 199664915-[(6-Bromo-2-pyridyl)-methyl]-tetrahydrofuran-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
1.5 °C

Procedure

A solution of 490 mg of 5-(6-bromo-2-pyridyl)-4-oxo-pentanoic acid methyl ester in 20 ml of methanol is mixed under ice cooling with 72 mg of sodium borohydride and stirred for 1 hour at 0-3° C. Then, 2 ml of acetone is added, stirred for 1 more hour and the reaction mixture is evaporated to dryness. The residue is distributed between water and ethyl acetate, the organic phase is dried on sodium sulfate and concentrated by evaporation. 421 mg of 5-[(6-bromo-2-pyridyl)-methyl]-tetrahydrofuran-2-one is obtained as yellow oil.

Workup

  1. stirringstirred for 1 more hour
  2. customthe reaction mixture is evaporated to dryness
  3. customthe organic phase is dried on sodium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9ebf860b826341cd9a1c7c947556ae6d
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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