Hydrochloric Acid → HCID 57228075, compound

HRID 1492925Notes

Reaction equation

HRID 1492925 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][CH:7]=[C:8]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=1.[H-].[Na+].Cl.CN(C)[CH:21]=[O:22]>C(OC)=O>[CH3:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][CH:7]=[C:8]([C:9](=[CH:21][OH:22])[C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 2824092Benzo[b]thiophene-3-acetic acid, 5-methyl-, methyl ester

Product 1

HCID 57228075HCID 57228075, compound

Reagents, catalysts & solvents 1

HCID 7865Methyl formateSolvent

Procedure

A solution of 79.7 g of methyl 5-methyl-3-benzo[b]thienylacetate in 200 ml of dimethylformamide and 200 ml of methyl formate is slowly added dropwise to a suspension of 10.4 g of sodium hydride in 100 ml of dimethylformamide. The reaction mixture is stirred for 2 hours at room temperature and then acidified with dilute hydrochloric acid, and this is then extracted with ethyl acetate. The organic phase is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. In this manner, methyl α-(5-methyl-3-benzo[b]thienyl)-β-hydroxyacrylate is obtained as the crude product which is used unpurified as the starting material in the next process step.

Workup

  1. extractionthis is then extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aba1dad1acfc4343b46d865e4eafaa03
Source dataset
uspto-grants-1994_12
Patent number
US05376677

Reaction notes

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