Water → 2-(alpha-Ethoxycarbonyl-benzylidene)-1-methylpyrrolidine

HRID 1278047Notes

Reaction equation

HRID 1278047 reaction equation
[Na].CN(C)[C:4]1[CH2:8][CH2:7][CH2:6][N+:5]=1[CH3:9].COS([O-])(=O)=O.[CH2:17]([O:19][C:20](=[O:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:18].O>C(O)C.CCOCC>[CH2:17]([O:19][C:20]([C:21](=[C:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH3:9])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:28])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 7590Ethyl phenylacetateHCID 5360545SodiumHCID 1784830372-Dimethylamino-1-methyl-1-pyrrolinium methylsulfate

Product 1

HCID 536395422-(alpha-Ethoxycarbonyl-benzylidene)-1-methylpyrrolidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Add a solution of 6.9 g of sodium in 140 ml of ethanol dropwise at 90°, with stirring, in a stream of nitrogen, to 84 g of 2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate and 37.9 g of phenylacetic acid ethyl ester. Stir the thus-prepared reaction mixture for a further 30 minutes at 90° and then distribute it between water and diethyl ether (300 ml of each). Isolate the product from the ether phase and distil it to obtain a yield of 48 g (85% of theory) of title compound (b.p. 106° to 107° at 0.008 mm of Hg).

Workup

  1. customthe thus-prepared reaction mixture for a further 30 minutes at 90°
  2. customdistil it

Sources & evidence

ORD record
ord-0111a7bde27c4b0d814c491e65b334c2
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

Loading…