Water → HCID 20353493, compound

HRID 372040Notes

Reaction equation

HRID 372040 reaction equation
[C:1](O)(=[O:4])[CH2:2][OH:3].C[Na].[CH2:8]([O:10][CH:11]([O:18][CH2:19][CH3:20])/[CH:12]=[CH:13]/[C:14]([O:16][CH3:17])=[O:15])[CH3:9].O>CS(C)=O>[CH2:19]([O:18][CH:11]([O:10][CH2:8][CH3:9])[CH:12]1[CH:13]([C:14]([O:16][CH3:17])=[O:15])[C:2](=[O:3])[CH2:1][O:4]1)[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 13899098HCID 13899098, compoundHCID 178526003HCID 178526003, compound

Product 1

HCID 20353493HCID 20353493, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The starting material is prepared as follows: To the suspension of 7.15 g of methyl sodium glycolate in 50 ml of dimethylsulfoxide and 25 ml of diemthylformamide, cooled to 0°, are added at once 9.5 g of methyl 4,4-diethoxy-crotonate and the mixture is stirred at room temperature for 3 hours. It is poured into water, washed with diethyl ether and the aqueous layer is acidified with cold N hydrochloric acid. It is extracted twice with diethyl ether, the extract dried, evaporated and the residue distilled, to yield the methyl 2-diethoxymethyl-4-oxo-tetrahydrofuran-3-carboxylate boiling at 123°-126°/0.5 mm Hg.

Workup

  1. customThe starting material is prepared
  2. temperaturecooled to 0°
  3. washwashed with diethyl ether
  4. extractionIt is extracted twice with diethyl ether
  5. customthe extract dried
  6. customevaporated
  7. distillationthe residue distilled

Sources & evidence

ORD record
ord-9b52d6c3d2f749be8139d010207b842f
Source dataset
uspto-grants-1978_05
Patent number
US04088779

Reaction notes

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