Benzyl Alcohol → 5-(benzyloxy)-2,3-dihydro-1H-inden-1-one

HRID 1678571Notes

Reaction equation

HRID 1678571 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(P(CCCC)CCCC)CCC>O1CCCC1>[C:13]1([CH2:12][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH2:6][CH2:5]3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 13831TributylphosphineHCID 2331475-Hydroxy-1-indanone

Product 1

HCID 107524065-(benzyloxy)-2,3-dihydro-1H-inden-1-oneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dihydro-5-hydroxy-1H-inden-1-one (1.0 g, 6.2 mmol), benzyl alcohol (0.65 g, 5.6 mol) and tributylphosphine (1.7 g, 8.4 mmol) in tetrahydrofuran (30 mL) was added 1,1′-(azocarbonyl)dipiperidine (2.1 g, 8.4 mmol), and the mixture was stirred at room temperature for 16 hours. Insolubles were filtered off, and then the filtrate was concentrated. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=10:1) to give the title compound (1.3 g, yield 97%) as powders.

Workup

  1. filtrationInsolubles were filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-0c206224660b4318914948726c13d809
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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