Sodium borohydride → HCID 178450342, compound

HRID 620109Notes

Reaction equation

HRID 620109 reaction equation
[BH4-].[Na+].[C:3]([C:8]1[C:9](=[O:17])[CH2:10][CH:11]([CH:15]=[O:16])[CH2:12][C:13]=1[OH:14])(=[O:7])[CH2:4][CH2:5][CH3:6]>O1CCCC1.O>[C:3]([C:8]1[C:13](=[O:14])[CH2:12][CH:11]([CH2:15][OH:16])[CH2:10][C:9]=1[OH:17])(=[O:7])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178450341HCID 178450341, compound

Product 1

HCID 178450342HCID 178450342, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

0.1 g of sodium borohydride was added to 2.0 g of 2-butyryl-5-formyl-3-hydroxycyclohex-2-en-1-one in 30 ml of aqueous tetrahydrofuran; the mixture was stirred for 2 hours at 25° C. The mixture was then diluted with water, extracted several times with diethyl ether, dried and concentrated. There was obtained 1.5 g of 2-butyryl-3-hydroxy-5-hydroxymethylcyclohex-2-en-1-one (compound no. 3).

Workup

  1. extractionextracted several times with diethyl ether
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6582df75176641e7aaa48ceb1e43d126
Source dataset
uspto-grants-1989_04
Patent number
US04820331

Reaction notes

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