Water → HCID 13907273, compound

HRID 2291631Notes

Reaction equation

HRID 2291631 reaction equation
[OH:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S(=O)(=O)(O)O.O.Cl[CH2:26]Cl>CO>[OH:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([CH2:8][CH2:9][C:10]([O:12][CH3:26])=[O:11])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 1283563-(4-Hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)propanoic acid

Product 1

HCID 13907273HCID 13907273, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(4-hydroxy-5-oxo-3-phenyl2,5-dihydro-2-furyl)propionic acid (3.85 g) in dry methanol (60 ml) was added conc. sulfuric acid (3.8 ml) in one portion at 5° C. After stirring for 3 hours at ° C., the mixture was poured into a mixture of water (100 ml) and dichloromethane (50 ml). The aqueous layer was extracted with dichloromethane (50 ml) once again. The combined organic layers were washed with water three times, dried, and evaporated to dryness. To the residue was added diethyl ether and the solid was collected by filtration to yield methyl 3-(4-hydroxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionate (3.49 g).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (50 ml) once again
  2. washThe combined organic layers were washed with water three times
  3. customdried
  4. customevaporated to dryness
  5. additionTo the residue was added diethyl ether
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-b520146f56914f73b8e2c160e5691fae
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

Loading…