Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:32])[CH2:6][CH2:7][C:8]([C:30]#[N:31])([C:15]1[C:23]2[C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[O:20][C:19]=2[C:18]([O:28][CH3:29])=[CH:17][CH:16]=1)[CH2:9][CH2:10][C:11](OC)=[O:12]>COCOC>[CH3:3][O:4][C:5]([CH:6]1[CH2:7][C:8]([C:30]#[N:31])([C:15]2[C:23]3[C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[O:20][C:19]=3[C:18]([O:28][CH3:29])=[CH:17][CH:16]=2)[CH2:9][CH2:10][C:11]1=[O:12])=[O:32]Participants
4
Procedure
To a mixture of 50% NaH (4.6 g, 0.097 mol) in dimethoxymethane (20 ml) at room temperature under nitrogen was added drop wise at room temperature and under nitrogen a solution of 4-cyano-4-(4-methoxy-dibenzofuran-1-yl)-heptane dioic acid dimethyl ester (13.3 g, 0.032 mol) in dimethoxymethane (130 ml). The reaction mass was allowed to stir for 3 hrs at room temperature. Once product is formed, the reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated under vacuum. 5-cyano-5-(4-methoxy-dibenzofuran-1-yl)-2-oxo-cyclohexane carboxylic acid methyl ester was isolated by column chromatography. Yield 9.8 g (80%)
Workup
- additionwas added drop wise at room temperature
- customOnce product is formed
- customthe reaction mass was quenched with water
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried with sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-d24369df3685419894a4c82fb5df0624
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263648B2
Linked notes
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