Sodium borohydride → HCID 14425608, compound

HRID 981425Notes

Reaction equation

HRID 981425 reaction equation
[CH3:1][C:2]1([CH3:23])[C:10]2[C:5](=[CH:6][C:7](/[C:11](/[CH3:19])=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([CH3:21])([CH3:20])[C:3]1=[O:22].[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1([CH3:23])[C:10]2[C:5](=[CH:6][C:7](/[C:11](/[CH3:19])=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([CH3:21])([CH3:20])[CH:3]1[OH:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14425607HCID 14425607, compound

Product 1

HCID 14425608HCID 14425608, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.4 g of 1,1,3,3-tetramethyl-5-[(E)-α-methylstyryl]2-indanone are dissolved in 100 ml of ethanol and treated at room temperature with 6 g of sodium borohydride. After stirring at room temperature for 16 hours the reaction mixture is poured on to ice and extracted repeatedly with ether. The organic phase is washed with saturated sodium chloride solution dried and evaporated. The residue can be recrystallized from hexane and gives 1.1 g of 1,1,3,3-tetramethyl-5-[(E)-α-methylstyryl]-2-indanol in colourless crystals, melting point 63°-67°.

Workup

  1. additionis poured on to ice
  2. extractionextracted repeatedly with ether
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. customdried
  5. customevaporated
  6. customThe residue can be recrystallized from hexane

Sources & evidence

ORD record
ord-b5f617be7e25457f84a555687bc931f5
Source dataset
uspto-grants-1991_02
Patent number
US04990703

Reaction notes

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