Sodium borohydride → HCID 14425608, compound

HRID 2107860Notes

Reaction equation

HRID 2107860 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-bcf3ceffc7cd400c81f5fc884fe3f79a
Source dataset
uspto-grants-1990_06
Patent number
US04935560

Reaction notes

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