Methanol → Norbornylfulvene

HRID 992785Notes

Reaction equation

HRID 992785 reaction equation
[CH2:1]1[CH:5]2[CH2:6][C:7](=O)[CH:3]([CH2:4]2)[CH2:2]1.[CH3:9][O-].[Na+].CO.[CH:14]1[CH2:18][CH:17]=[CH:16][CH:15]=1>C(OCC)C.O>[C:3]12([C:15]3[C:14](=[CH2:9])[CH:18]=[CH:17][CH:16]=3)[CH2:4][CH:5]([CH2:6][CH2:7]1)[CH2:1][CH2:2]2

Participants

7

Reactant 4

HCID 887MethanolHCID 7612CyclopentadieneHCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 10942334Sodium Methoxide

Product 1

HCID 86588813Norbornylfulvene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Norcamphor (10.00 g, 90.8 mmol) and sodium methoxide (12.0 g, 222 mmol) and 100 mL methanol were added to a 250 mL flask. The solids were dissolved before addition of cyclopentadiene (12.0 g, 182 mmol). After stirring for 68 hours, 200 mL water and 100 mL diethyl ether were added to the deep red solution. The organic layer was isolated and the aqueous layer was extracted with diethyl ether (3×50 mL). The combined organic layers were dried over MgSO4, filtered and rotavapped to yield the crude product in quantitative yield.

Workup

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

Sources & evidence

ORD record
ord-068c71c08c4040b6b5dcb51961ae0e8f
Source dataset
uspto-grants-2002_10
Patent number
US06469188B1

Reaction notes

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