Reaction equation
C(CCC([CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)C(O)=O)#N.[CH2:20]([O:22][C:23](=[O:34])[CH:24]([CH2:30][CH2:31][C:32]#[N:33])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH3:21].[H-].[Na+].ClCC1C2C(=CC=CC=2)C=CC=1>CN(C=O)C>[CH2:28]([O:27][C:25](=[O:26])[C:24]([CH2:30][CH2:31][C:32]#[N:33])([CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[C:23]([O:22][CH2:20][CH3:21])=[O:34])[CH3:29]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Cyano-2(R,S)-α-naphthylmethylbutyric acid: 2.13 g of 2-cyanoethylmalonic acid diethyl ester are added to a suspension of 0.48 g of sodium hydride dispersion in 25 ml of DMF. The reaction mixture is stirred for 2 hours at 80° and then, at room temperature, 1.77 g of α-chloromethylnaphthalene in 5 ml of DMF are added. The mixture is further stirred for 16 hours at 50° and then concentrated by evaporation. The residue is dissolved in ethyl acetate, washed with 0.1N hydrochloric acid and water, dried over sodium sulphate and concentrated by evaporation, leaving 2-cyanoethyl-α-naphthylmethylmalonic acid diethyl ester.
Workup
- stirringThe mixture is further stirred for 16 hours at 50°
- concentrationconcentrated by evaporation
- dissolutionThe residue is dissolved in ethyl acetate
- washwashed with 0.1N hydrochloric acid and water
- dry with materialdried over sodium sulphate
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-e0ff61d3b6514a55bc0cf587e046c10f
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04727060
Linked notes
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