Ethanol → 2-Ethoxycarbonylacetyl-3-hydroxy-thiophene

HRID 1589978Notes

Reaction equation

HRID 1589978 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[OH:9])(=[O:3])[CH3:2].[Na].C(O)C.[C:14](=O)([O:18]CC)[O:15][CH2:16][CH3:17]>>[CH2:16]([O:15][C:14]([CH2:2][C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[OH:9])=[O:3])=[O:18])[CH3:17]

Participants

5

Reactant 4

HCID 702EthanolHCID 7766Diethyl CarbonateHCID 5360545Sodium2×HCID 133523522-Acetyl-3-hydroxythiophene

Product 1

HCID 148376412-Ethoxycarbonylacetyl-3-hydroxy-thiophene

Procedure

4.8 g (0.0337 mol) of 2-acetyl-3-hydroxythiophene in 150 ml of diethyl carbonate are heated to 90°-100° C. 5 g of small sodium pieces are then added. Stirring is continued for 15 hours at 90°-100° C. To decompose remainders of sodium, a little ethanol is added. For working up, the mixture is extracted twice using 75 ml of water, the aqueous phase is then acidified with 10 ml of concentrated HCl, extracted 3 times with 50 ml portions of ether, dried, distilled in vacuo, and the fraction between 70° and 100° C. (0.6 mbar, educt) and between 113° and 118° C. (0.4 mbar product) is collected.

Workup

  1. extractionthe mixture is extracted twice
  2. extractionextracted 3 times with 50 ml portions of ether
  3. customdried
  4. distillationdistilled in vacuo
  5. customthe fraction between 70° and 100° C. (0.6 mbar, educt) and between 113° and 118° C. (0.4 mbar product) is collected

Sources & evidence

ORD record
ord-810244996f3048c2870fa8b010ac7586
Source dataset
uspto-grants-1993_04
Patent number
US05201936

Reaction notes

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