4-Bromo-7a-methyl-hexahydro-indene-1,5-dione → 4-Allyloxy-7a-methyl-hexahydro-indene-1,5-dione

HRID 2358270Notes

Reaction equation

HRID 2358270 reaction equation
Br[CH:2]1[C:10](=[O:11])[CH2:9][CH2:8][C:7]2([CH3:12])[CH:3]1[CH2:4][CH2:5][C:6]2=[O:13]>C(O)C=C>[CH2:10]([O:11][CH:2]1[C:10](=[O:11])[CH2:9][CH2:8][C:7]2([CH3:12])[CH:3]1[CH2:4][CH2:5][C:6]2=[O:13])[CH:9]=[CH2:8]

Participants

3

Reactant 1

HCID 141132994-Bromo-7a-methyl-hexahydro-indene-1,5-dione

Product 1

HCID 684575234-Allyloxy-7a-methyl-hexahydro-indene-1,5-dione

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent

Procedure

To the stirred suspension of 4-bromo-7a-methyl-hexahydro-indene-1,5-dione 1 (prepared according to the procedure described in J. Org. Chem. 2001, 66, 626.) (2.44 g, 10 mmol), molecular sieves of 4 Å (2.5 g) and silica gel (2.5 g) in allyl alcohol (20 mL) was added Ag2O (2.55 g, 11 mmol) at room temperature. The reaction mixture was stirred at room temperature in the dark for 8 h. The reaction mixture was filtered through a mixture of Celite® and silica gel. The solvent was removed under reduced pressure to yield the title compound as a crude yellow oil.

Workup

  1. customprepared
  2. filtrationThe reaction mixture was filtered through a mixture of Celite® and silica gel
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-86f823d3f7ed40d1b438dae46a6f298b
Source dataset
uspto-grants-2010_07
Patent number
US07763648B2

Reaction notes

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