Hydrochloric Acid → HCID 12689096, compound

HRID 544158Notes

Reaction equation

HRID 544158 reaction equation
CN([CH:4]=[C:5]([C:14](=[O:16])[CH3:15])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])C.[C:17](OCC)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].[O-]CC.[Na+].[Na].Cl>C(O)C.O>[C:6]([C:5]1[C:14](=[O:16])[CH:15]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:23][CH:4]=1)(=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 54257685HCID 54257685, compound

Product 1

HCID 12689096HCID 12689096, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of this enamine (19.0 g) and diethyl oxalate (23.7 ml) in ethanol (120 ml) was added to a solution of sodium ethoxide prepared by dissolving sodium (3.0 g) in ethanol (60 ml). The solution was stirred for 6 hours at room temperature then acidified with 5 M hydrochloric acid solution (100 ml). The mixture was allowed to stand overnight and was then cooled and diluted with water (300 ml) to give pale crystals of ethyl 5-benzoyl-4-oxo-4H-pyran-2-carboxylate (mp 84°-86° C.).

Workup

  1. customprepared
  2. waitto stand overnight
  3. temperaturewas then cooled

Sources & evidence

ORD record
ord-0817b42fa8a14786a67d07b3fdbdf715
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

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