Water → HCID 23157557, compound

HRID 507979Notes

Reaction equation

HRID 507979 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][C:13]2=[O:18].[BH4-].[Na+].O>O1CCCC1.CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][CH:13]2[OH:18]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23157344HCID 23157344, compound

Product 1

HCID 23157557HCID 23157557, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(2,6-Dimethylphenyl)indan-1-one (2.00 g, 8.47 mmol) was dissolved in a mixture of tetrahydrofuran (20 mL) and methanol (10 mL), sodium borohydride (449 mg, 11.9 mmol) was added, and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-60% ethyl acetate/hexane) to give the title compound (1.54 g, yield 76%) as a colorless oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe extract was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (5%-60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d1f0e4165c3c47d79d26112fc162bcb8
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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