Water → Methyl 2-(3-formyl-2-thienylthio)acetate

HRID 1382363Notes

Reaction equation

HRID 1382363 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[S:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+].O>CC(C)=O.CCOCC>[CH:2]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[S:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:1]

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 14460450Methyl [3-(2-dioxolanyl)-thiophene-2-ylthio]acetate

Product 1

HCID 11959090Methyl 2-(3-formyl-2-thienylthio)acetateYield 101.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl [3-(2-dioxolanyl)-thiophene-2-ylthio]acetate (23.36 g) in acetone (100 mL) was added p-toluenesulfonic acid (0.25 g) and the reaction mixture was stirred at room temperature for 1 hour. A saturated aqueous solution of sodium bicarbonate (4 mL) was added with stirring followed by the addition of water (50 mL). After stirring for 10 minutes, the acetone was evaporated in vacuo to leave a gum and water. The gum was dissolved in ether (500 mL) and extracted with water (4×50 mL), dried (MgSO4), filtered and the solvent was evaporated in vacuo to leave 19.77 g of oily methyl (3-formylthiophene-2-ylthi-o)acetate which was used in the next step without purification.

Workup

  1. stirringwith stirring
  2. stirringAfter stirring for 10 minutes
  3. customthe acetone was evaporated in vacuo
  4. customto leave a gum and water
  5. extractionextracted with water (4×50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-817f9dff5f094c1a98c4fe7d898e7d91
Source dataset
uspto-grants-1989_02
Patent number
US04806562

Reaction notes

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