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

HRID 2422207Notes

Reaction equation

HRID 2422207 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 mixture of tetrahydrofuran (20 mL) and methanol (10 mL), sodium borohydride (0.41 g, 11 mmol) was added, and the mixture was stirred at room temperature for 2 hrs. 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 (hexane/ethyl acetate=3:1) to give the title compound (1.16 g, yield 89%) as a white powder.

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 (hexane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-abe4a95ad03345bda0e6021a77e03274
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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