Hydrochloric Acid → HCID 57977387, compound

HRID 505369Notes

Reaction equation

HRID 505369 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[CH3:9][C:10]1[CH:14]=[CH:13][S:12][C:11]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17].Cl>C1(C)C=CC=CC=1.CO>[CH3:9][C:10]1[CH:14]=[CH:13][S:12][C:11]=1[CH:15]([C:3]([O:6][CH3:7])=[O:8])[C:16]([O:18][CH3:19])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 54208925HCID 54208925, compound

Product 1

HCID 57977387HCID 57977387, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Under argon, 14.7 g of sodium hydride (60% in mineral oil) were added to 311 ml (332 g, 3.685 mol) of dimethyl carbonate, and the mixture was heated to 80° C. A solution of 41 g (0.217 mol) of methyl (3-methylthiophen-2-yl)acetate in 50 ml of toluene was slowly added dropwise at this temperature, and the mixture was stirred at reflux overnight. For work-up, the mixture was diluted with about 200 ml of methanol, poured into ice-water and acidified with dilute hydrochloric acid. Extraction with dichloromethane, drying of the organic phase over sodium sulphate, filtration and removal of the solvent gave 43.6 g of dimethyl 2-(3-methylthiophen-2-yl)malonate. Yield: 88%. 1H-NMR (DMSO): δ=7.42 (d, 1H), 6.89 (d, 1H), 5.27 (s, 1H), 3.69 (s, 6H), 2.15 (s, 3H).

Workup

  1. temperatureat reflux overnight
  2. extractionExtraction with dichloromethane
  3. dry with materialdrying of the organic phase over sodium sulphate, filtration and removal of the solvent

Sources & evidence

ORD record
ord-7e40cd67015748ae9b71f138515b1e57
Source dataset
uspto-grants-2010_08
Patent number
US07781439B2

Reaction notes

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