Acetone → 3-(2-Norbornyl)-6,6-dimethylfulvene

HRID 2120941Notes

Reaction equation

HRID 2120941 reaction equation
[CH3:1][O-].[Na+].[C:4]12([C:11]3[CH2:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][CH2:5]2.[CH3:16][C:17](C)=O.O>CO.C(OCC)C>[CH:15]12[CH2:14][CH:13]([CH2:16][CH2:17]1)[CH2:12][CH:11]2[C:4]1[CH:9]=[CH:8][C:7](=[C:6]([CH3:5])[CH3:1])[CH:10]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 10942334Sodium MethoxideHCID 23436666HCID 23436666, compound

Product 1

HCID 234366713-(2-Norbornyl)-6,6-dimethylfulvene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium methoxide (4.00 g, 74.0 mmol) was added to a solution of norbornylcyclopentadiene (8.00 g, 49.9 mmol) in 50 mL methanol. Acetone (15.8 g, 270 mmol) was added and the reaction stirred for 48 hours when 200 mL water and 100 mL diethyl ether were added. The organic layer was isolated and the aqueous layer was extracted with diethyl ether (4×50 mL). The organic layers were dried over MgSO4, filtered, and rotavapped to provide the crude product as a yellow oil, which was purified by in vacuo drying and passing through a short column of alumina: 8.18 g (81.8%). MS (GC-MS) m/z 200.3 (M+).

Workup

  1. additionwere added
  2. customThe organic layer was isolated
  3. extractionthe aqueous layer was extracted with diethyl ether (4×50 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-caa92e04b30c42d891fea6f13d41a0e3
Source dataset
uspto-grants-2004_02
Patent number
US06693153B2

Reaction notes

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