Water → HCID 54504210, compound

HRID 1278040Notes

Reaction equation

HRID 1278040 reaction equation
[Na].COS([O-])(=O)=O.CN(C)[C:10]1[CH2:14][CH2:13][CH2:12][N+:11]=1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:23]([O:25][C:26](=[O:38])[CH2:27][C:28]1[CH:37]=[CH:36][C:33]([O:34][CH3:35])=[C:30]([O:31][CH3:32])[CH:29]=1)[CH3:24].O>C(O)C.C(OCC)C>[CH2:15]([N:11]1[CH2:12][CH2:13][CH2:14][C:10]1=[C:27]([C:26]([O:25][CH2:23][CH3:24])=[O:38])[C:28]1[CH:37]=[CH:36][C:33]([O:34][CH3:35])=[C:30]([O:31][CH3:32])[CH:29]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 87441Ethyl 3,4-dimethoxyphenylacetateHCID 5360545SodiumHCID 178483029HCID 178483029, compound

Product 1

HCID 54504210HCID 54504210, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Add (dropwise at 90°, with stirring, in a stream of nitrogen) a solution of 2.6 g of sodium in 50 ml of ethanol to 34.5 g of 2-dimethylamino-1-benzyl-1-pyrroliniummethylsulfate and 19.7 g of homoveratric acid ethyl ester. Keep the resulting reaction mixture at this temperature for a further 30 minutes and then distribute it between water and diethyl ether. Dry the ether solution over sodium sulfate and then concentrate it to obtain a yield [32.2 g (96% of theory)] of title compound.

Workup

  1. additionAdd (dropwise at 90°
  2. customthe resulting reaction mixture at this temperature for a further 30 minutes
  3. dry with materialDry the ether solution over sodium sulfate
  4. concentrationconcentrate it
  5. customto obtain

Sources & evidence

ORD record
ord-250d87d96f8449d2b2e97c81c080b393
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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