Sodium borohydride → HCID 20203303, compound

HRID 978460Notes

Reaction equation

HRID 978460 reaction equation
[O:1]=[C:2]([CH3:11])[CH2:3][CH2:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.[BH4-].[Na+]>C(O)C>[OH:1][CH:2]([CH3:11])[CH2:3][CH2:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12477271HCID 12477271, compound

Product 1

HCID 20203303HCID 20203303, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(4-Oxopentyl)thiophene (3.30 g, 19.6 mmol) was dissolved in 10 ml of 95% ethanol and the solution was added to a stirred solution of sodium borohydride (0.38 g, 10 mmol) in 20 ml of ethanol at room temperature. The mixture was stirred overnight and the excess reducing agent destroyed by the dropwise addition of 1N HCl. The solvents were evaporated and the residue partitioned between water and ether. The organic phase was washed with water and brine and dried (Na2SO4) Evaporation of the solvents gave 3.13 g of product as a yellow oil, which was used without purification in the next step.

Workup

  1. customdestroyed by the dropwise addition of 1N HCl
  2. customThe solvents were evaporated
  3. customthe residue partitioned between water and ether
  4. washThe organic phase was washed with water and brine
  5. customdried
  6. custom(Na2SO4) Evaporation of the solvents

Sources & evidence

ORD record
ord-ced00bfdcd9c41c4a727bc81d7eeaaf7
Source dataset
uspto-grants-1987_05
Patent number
US04665090

Reaction notes

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