Sodium borohydride → HCID 68694744, compound

HRID 2236904Notes

Reaction equation

HRID 2236904 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([N:6]2[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][C:7]2=[O:14])=[CH:2]1.[BH4-].[Na+]>CO>[OH:13][CH2:12][C:9]1[CH:10]=[CH:11][N:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[C:7](=[O:14])[CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86619603HCID 86619603, compound

Product 1

HCID 68694744HCID 68694744, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-thiophen-3-yl-2-oxo-1,2-dihydro-pyridine-4-carbaldehyde (0.27 g, 1.3 mmol) in methanol (20 mL) is cooled to 0° C. in an ice-water bath and then treated with sodium borohydride (50 mg, 1.3 mmol). After stirring at 0° C. for two hours, the reaction mixture is quenched by the addition of 10% aqueous hydrochloric acid. The mixture is extracted with ethyl acetate. The combined organic extracts were washed once with saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure to provide 4-hydroxymethyl-1-thiophen-3-yl-1H-pyridin-2-one (0.18 g, 67%), which is used in the following step without further purification.

Workup

  1. customthe reaction mixture is quenched by the addition of 10% aqueous hydrochloric acid
  2. extractionThe mixture is extracted with ethyl acetate
  3. washThe combined organic extracts were washed once with saturated aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-030652ad86f24d9b88bae303173649ea
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…