Reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:20])[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:10]2[CH:9]=[C:8]([CH2:16][C:17]([OH:19])=[O:18])[CH:7]=[CH:6][C:5]1=2.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C>[CH3:3][C:4]1([CH3:20])[CH2:13][CH2:12][C:11]([CH3:14])([CH3:15])[C:10]2[CH:9]=[C:8]([CH2:16][C:17]([O:19][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:18])[CH:7]=[CH:6][C:5]1=2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
730 mg (0.024 mol) of sodium hydride (80 and 100 ml of DMF were introduced into a three-necked flank under a nitrogen stream. A solution of 5 g (0.02 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetic acid in 40 ml of DMF was added dropwise and the mixture was stirred until the gaseous emission ceased. 2.9 ml (0.024 mol) of benzyl bromide were then added and the mixture was stirred at room temperature for 4 hours. The reaction medium was poured into water, and extracted with ethyl acetate. The organic phase was decanted off, dried over magnesium sulfate and evaporated. 6.7 g (100%) of the expected ester were recovered in the form of a slightly yellow oil.
Workup
- stirringthe mixture was stirred at room temperature for 4 hours
- extractionextracted with ethyl acetate
- customThe organic phase was decanted off
- dry with materialdried over magnesium sulfate
- customevaporated
- custom6.7 g (100%) of the expected ester were recovered in the form of a slightly yellow oil
Sources & evidence
- ORD record
- ord-ef9d103de7344601a737fc0d84aab076
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05709867
Linked notes
Loading…