Acetone → 3-(1-Methyl-1-cyclohexyl)-6,6-dimethylfulvene
Reaction equation
[CH3:1][C:2]1([C:8]2[CH2:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:13][C:14]([CH3:16])=O.N1CCCC1>CO.CCOCC.O>[CH3:1][C:2]1([C:8]2[CH:12]=[CH:11][C:10](=[C:14]([CH3:16])[CH3:13])[CH:9]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1Participants
Procedure
To a solution of 2.71 g (16.7 mmol) of (1-methyl-1-cyclohexyl)cyclopentadiene in 30 ml of methanol, 25 ml (340.5 mmol) of acetone and 2.8 ml (33.5 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for 3 days. After the reaction solution was diluted with 100 ml of ether, 50 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was isolated and purified by column chromatography (silica gel, developing solvent: hexane) to obtain 2.95 g (14.58 mmol) of a yellow liquid (yield: 87%). The analyzed values are given below.
Workup
- additionwas added
- customThe organic phase was separated
- washwashed with water
- dry with materiala saturated saline solution, then dried over anhydrous magnesium sulfate
- filtrationfiltered
- customFrom the filtrate, the solvent was removed under reduced pressure
- customto obtain a liquid
- customThe liquid was isolated
- custompurified by column chromatography (silica gel, developing solvent: hexane)
Sources & evidence
- ORD record
- ord-9e7ea9585996434eafaa9b2815ea51f1
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06939928B1
Reaction notes
Loading…