Water → 5-(benzyloxy)-2,3-dihydro-1h-inden-1-ol

HRID 1678572Notes

Reaction equation

HRID 1678572 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[CH2:13][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>O1CCCC1.CO>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH:14]([OH:18])[CH2:13][CH2:12]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 107524065-(benzyloxy)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 2552285-(benzyloxy)-2,3-dihydro-1h-inden-1-olYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,3-Dihydro-5-(phenylmethoxy)-1H-inden-1-one (1.3 g, 5.46 mmol) was dissolved in a mixed solution of tetrahydrofuran (20 mL) and methanol (10 mL). Sodium borohydride (0.41 g, 11 mmol) was added thereto, and then the mixture was stirred at room temperature for 2 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=3:1) to give the title compound (1.16 g, yield 89%) as white powders.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-e80aaaa14d054af580434b8bef913cc1
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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