Diethyl Oxalate → HCID 131720351, compound

HRID 1939343Notes

Reaction equation

HRID 1939343 reaction equation
[C:1]([C:4]1[C:9]2[O:10][CH2:11][C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[C:14](=[O:15])[C:8]=2[CH:7]=[CH:6][C:5]=1[OH:20])(=[O:3])[CH3:2].[Na].[C:22](OCC)(=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(O)C>[CH2:26]([O:25][C:23]([C:22]1[O:20][C:5]2[CH:6]=[CH:7][C:8]3[C:14](=[O:15])[C:13]4[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=4[CH2:11][O:10][C:9]=3[C:4]=2[C:1](=[O:3])[CH:2]=1)=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 5360545SodiumHCID 21467595HCID 21467595, compound

Product 1

HCID 131720351HCID 131720351, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.04 g (30 mmol) 4-acetyl-6,11-dihydro-3-hydroxydibenz[b,e]oxepin-11-one is added to a solution of 4.14 g (180 mmol) sodium in 250 ml ethanol, it is heated for 10 minutes to reflux, cooled to room temperature, admixed with 14.6 g (100 mmol) diethyl oxalate, heated for 90 minutes to reflux, allowed to cool and filtered. The precipitate is taken up in 100 ml ethanol, the suspension is saturated with hydrogen chloride and subsequently heated for 1 hour to 50° C. After cooling it is poured onto ice and filtered. 7.8 g of the title compound (74% of theory) of melting point 178°-180° C. (from ethanol) remain.

Workup

  1. temperatureis heated for 10 minutes
  2. temperatureto reflux
  3. temperatureheated for 90 minutes
  4. temperatureto reflux
  5. temperatureto cool
  6. filtrationfiltered
  7. temperaturesubsequently heated for 1 hour to 50° C
  8. temperatureAfter cooling it
  9. additionis poured onto ice
  10. filtrationfiltered

Sources & evidence

ORD record
ord-5a4667aed3454a40b3b5ed78bd1af4f6
Source dataset
uspto-grants-1997_12
Patent number
US05696155

Reaction notes

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