Triethylamine → (1RS,2SR,6RS,7SR)-5-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate
Reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[CH:17]1[C:25](=[O:26])[CH:24]2[CH:19]([CH:20]3[O:27][CH:23]2[CH2:22][CH2:21]3)[C:18]1=[O:28].C(N(CC)CC)C>ClCCl>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1]([O:26][C:25]1[CH:24]2[CH:19]([C:18](=[O:28])[C:17]=1[C:10]1[C:11]([CH3:16])=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=1[CH3:8])[CH:20]1[O:27][CH:23]2[CH2:22][CH2:21]1)=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of pivaloyl chloride (0.055 g, 0.57 mmol) in dichloromethane (2 ml) is added dropwise to a solution of (1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione (0.12 g, 0.42 mmol) in dichloromethane (2 ml) at room temperature and the reaction mixture is stirred for 2 minutes. A solution of triethylamine (0.08 ml) in dichloromethane (1 ml) is added and the reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with dichloromethane (20 ml) and washed with saturated aqueous sodium bicarbonate solution. The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure to give (1RS,2SR,6RS,7SR)-5-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate as a colourless oil.
Workup
- stirringthe reaction mixture is stirred at room temperature for 3 hours
- washwashed with saturated aqueous sodium bicarbonate solution
- dry with materialThe organic phase is dried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe filtrate evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-639ec45650af4875a545357d0ad21e8b
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754242B2
Reaction notes
Loading…