Furan → (1RS, 2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo[5.2.1.02,6]-dec-8-en-3,5-dione
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[I-].[Mg+2].[I-].[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:23][CH3:24])=[C:14]([CH:16]2[C:20](=[O:21])[CH:19]=[CH:18][C:17]2=[O:22])[CH:15]=1>ClCCl.CO>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:23][CH3:24])=[C:14]([CH:16]2[C:20](=[O:21])[CH:19]3[CH:18]([CH:5]4[O:1][CH:2]3[CH:3]=[CH:4]4)[C:17]2=[O:22])[CH:15]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Furan (4.0 ml, 55.0 mmol) and magnesium iodide (1.00 g, 3.6 mmol) are added to a solution of 2-(5-bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione (5.0 g, 17.9 mmol) in dichloromethane (20 ml) and the mixture is stirred at room temperature for 3 days. A further quantity of furan (1.3 ml, 17.8 mmol) is added and stirring continued for 18 hours, and then a further quantity of furan (1.3 ml, 17.8 mmol) is added and the mixture is stirred for 48 hours, and then allowed to stand at room temperature for 5 days. The reaction mixture is dissolved in methanol and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione.
Workup
- stirringstirring
- waitcontinued for 18 hours
- stirringthe mixture is stirred for 48 hours
- waitto stand at room temperature for 5 days
- concentrationconcentrated under reduced pressure
- customThe residue is purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-e71447e9acae4ebf9a8d37f13c152147
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754242B2
Reaction notes
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