Hydrochloric Acid → Ethyl 4-oxo-5-phenyl-4H-pyran-2-carboxylate

HRID 1902648Notes

Reaction equation

HRID 1902648 reaction equation
CN(C)[CH:3]=[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5](=[O:7])[CH3:6].[C:15](OCC)(=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].[O-]CC.[Na+].[Na].Cl>C(O)C.O>[O:7]=[C:5]1[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][O:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 14883693-Buten-2-one, 4-(dimethylamino)-3-phenyl-HCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 13091198Ethyl 4-oxo-5-phenyl-4H-pyran-2-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 4-dimethylamino-3-phenyl-3-buten-2-one (30.3 g) and diethyl oxalate (43.5 ml) in ethanol (75 ml) was added to a stirred solution of sodium ethoxide prepared by dissolving sodium (5.5 g) in ethanol (150 ml). The stirred mixture was heated under reflux for 1 hour, cooled to 20°-25° C. and acidified by addition of 5 N hydrochloric acid (150 ml). The mixture was stirred for a further hour, then cooled to 5° C., and diluted with water (300 ml). The solid title product was recrystallised from ethanol-water (mp 110°-112° C.).

Workup

  1. customprepared
  2. temperatureThe stirred mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperaturecooled to 20°-25° C.
  5. customThe solid title product was recrystallised from ethanol-water (mp 110°-112° C.)

Sources & evidence

ORD record
ord-8b945b078c7a48f7a3821f884eec6a20
Source dataset
uspto-grants-1982_12
Patent number
US04364956

Reaction notes

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