Diethyl Carbonate → HCID 23333808, compound

HRID 904231Notes

Reaction equation

HRID 904231 reaction equation
[Na].[CH3:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=1.[C:20](=O)([O:24]CC)[O:21][CH2:22][CH3:23]>C(O)C>[CH3:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:20]([O:21][CH2:22][CH3:23])=[O:24])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 5360545SodiumHCID 23333846HCID 23333846, compound

Product 1

HCID 23333808HCID 23333808, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.4 g (0.06 mole) of metallic sodium in 50 ml of ethanol was added 10 g (0.038 mole) of ethyl 4-(3-methyl-2-thienyl)phenylacetate [I.R. (liquid film): νC=O 1735 cm-1 ], followed by adding 14.3 g (0.121 mole) of diethyl carbonate. The mixture was stirred at 50° to 60° C. for 30 minutes and freed from the ethanol by distillation under reduced pressure. To the residue were added 15 ml of 1 N hydrochloric acid and 50 ml of benzene and the mixture was shaken thoroughly. The organic layer was dried over anhydrous magnesium sulfate and freed from the solvent by distillation under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: benzene/n-hexane=2/1) to obtain 7.8 g (58% yield) of oily diethyl [4-(3-methyl-2-thienyl)phenyl]malonate.

Workup

  1. distillationfreed from the ethanol by distillation under reduced pressure
  2. additionTo the residue were added 15 ml of 1 N hydrochloric acid and 50 ml of benzene
  3. stirringthe mixture was shaken thoroughly
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationfreed from the solvent by distillation under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developing solvent: benzene/n-hexane=2/1)

Sources & evidence

ORD record
ord-bb3bfc982b3e4350b2bfbe467b527cb1
Source dataset
uspto-grants-1980_10
Patent number
US04230719

Reaction notes

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