HCID 22621682, compound → HCID 22621659, compound
Reaction equation
Br[CH:2]1[CH2:4][C:3]1([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(C1(CCCCC)CC1)CCCC.CC(C)([O-])C.[K+]>CS(C)=O>[CH2:10]([C:3]1([CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:4]=[CH:2]1)[CH2:11][CH2:12][CH2:13][CH3:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
To a solution of 1.90 g of an equal mixture of 2-bromo-1,1-dipentyl-cyclopropane and 1,1-dipentyl-cyclopropane in 10 ml dimethylsulfoxide was added 0.818 g (0.00308 mol) of potassium t-butoxide. The resulting mixture was heated to 85° C. for 5 hours and then stirred at room temperature for 16 hours. To this was added 0.100 g of potassium t-butoxide. The resulting mixture was heated to 85° C. for 2 hours then cooled to room temperature. The reaction mixture was poured onto water and then extracted with diethyl ether. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo to yield 1.90 g of 3,3-dipentyl-cyclopropene mixed in equal parts with 1,1-dipentyl-cyclopropane as an oil.
Workup
- temperatureThe resulting mixture was heated to 85° C. for 2 hours
- temperaturethen cooled to room temperature
- additionThe reaction mixture was poured onto water
- extractionextracted with diethyl ether
- customThe resulting mixture was transferred to a separatory funnel
- customthe phases were separated
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- customThe solvent was removed from the filtrate in vacuo
Sources & evidence
- ORD record
- ord-4ce06228bd824381a5382d778ff8f332
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06365549B2
Reaction notes
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