Water → HCID 23436670, compound

HRID 992788Notes

Reaction equation

HRID 992788 reaction equation
[C:1]12([C:8]3[CH2:12][CH:11]=[CH:10][CH:9]=3)[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[C:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[O-].[Na+].O>C(O)C.C(OCC)C>[CH:2]12[CH2:3][CH:4]([CH2:5][CH2:6]1)[CH2:7][CH:1]2[C:8]1[CH:12]=[CH:11][C:10](=[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3102BenzophenoneHCID 10942334Sodium MethoxideHCID 23436666HCID 23436666, compound

Product 1

HCID 23436670HCID 23436670, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A 500 mL round bottom flask was charged with a solution of norbornylcyclopentadiene (7.39 g, 46.1 mmol) and benzophenone (8.41 g, 46.2 mmol) in 100 mL absolute ethanol. NaOMe (5.50 g, 102 mmol) was added and the orange solution was stirred for 61 days before 100 mL H2O and 100 mL diethyl ether were added. The organic layer was isolated and the aqueous layer was extracted with diethyl ether (2×50 mL). The combined organic layers were dried over MgSO4, filtered, and rotavapped to provide 14.88 grams of red oily material. This was subjected to Kugelrohr distillation under high vacuum at 80-100° C., leaving behind 9.30 grams of red oil. This was Kugelrohred at 100-160° C. to afford 7.05 grams of product as a viscous red oil (47.1%).

Workup

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

Sources & evidence

ORD record
ord-48553633e0a7451d89b79ee7d878580a
Source dataset
uspto-grants-2002_10
Patent number
US06469188B1

Reaction notes

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