Dimethyl Sulfoxide → HCID 53927843, compound

HRID 1492928Notes

Reaction equation

HRID 1492928 reaction equation
Br[CH2:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][CH:8]=[C:9]([C:10](=[CH:15][O:16][CH3:17])[C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=1.CS(C)=[O:22].C(=O)([O-])O.[Na+]>O>[CH:2]([C:3]1[CH:19]=[CH:18][C:6]2[S:7][CH:8]=[C:9]([C:10](=[CH:15][O:16][CH3:17])[C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=1)=[O:22]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 53960446HCID 53960446, compound

Product 1

HCID 53927843HCID 53927843, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2 g of methyl α-(5-bromomethyl-3-benzo[b]thienyl)-13-methoxyacrylate (see Example 11), 16 ml of dimethyl sulfoxide and 0.5 g of sodium hydrogencarbonate is heated at 85° C. for 2.5 hours. Water is subsequently added, and the mixture is extracted using ethyl acetate. The organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue is then purified by chromatography on silica gel using diethyl ether/n-hexane (2:1). Recrystallization from methylene chloride/n-hexane gives methyl α-(5-formyl-3-benzo[b]thienyl)-β-methoxyacrylate as colourless crystals, m.p. 134°-135° C.

Workup

  1. extractionthe mixture is extracted
  2. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue is then purified by chromatography on silica gel
  5. customRecrystallization from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-3ec4399c58784aa994322e85cfff6ba6
Source dataset
uspto-grants-1994_12
Patent number
US05376677

Reaction notes

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