Hydrochloric Acid → HCID 19606349, compound

HRID 1603905Notes

Reaction equation

HRID 1603905 reaction equation
[CH2:1]([S:8][CH2:9][C:10]1([C:19]([O:21]CC)=[O:20])[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(O)C>[CH2:1]([S:8][CH2:9][C:10]1([C:19]([OH:21])=[O:20])[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19606280HCID 19606280, compound

Product 1

HCID 19606349HCID 19606349, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of ethyl 2-benzylthiomethyl-2,3-dihydrobenzofuran-2-carboxylate (2.70 g, 8.53 mmol) in ethanol (100 ml) was added with a solution of 1M potassium hydroxide. (42.6 ml). The mixture was refluxed under stirring for 3 h, after that was neutralized with 1M HCl and ethanol was evaporated off under reduced pressure. The resulting crude was suspended in water (30 ml) and extracted with ethyl acetate (4×30 ml). The organic phase was dried and the solvent was evaporated off under reduced pressure, to obtain 2.172 g of the title compound as a brown solid with melting point 125-127° C. (85% yield).

Workup

  1. temperatureThe mixture was refluxed
  2. customwas evaporated off under reduced pressure
  3. extractionextracted with ethyl acetate (4×30 ml)
  4. customThe organic phase was dried
  5. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-19465cfe9fcf46639ece24201607c34d
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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