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

HRID 2352277Notes

Reaction equation

HRID 2352277 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:7][CH:8]=[CH:9][C:10]=1[S:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].C(=O)(O)[O-].[Na+].O>CCOCC>[CH:2]([C:6]1[S:7][CH:8]=[CH:9][C:10]=1[S:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 15698034Methyl 3-[2-(2-dioxolanyl)thiophene-3-yl]-3-thiapropionate

Product 1

HCID 12475298Methyl (2-formyl-3-thienylthio)acetateYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl-3-[2-(2-dioxolanyl)thiophene-3-yl]-3-thiapropionate (4) (117.63 g, 0.515 mole) was dissolved in actone (500 mL), and p-tolunesulfonic acid hydrate (1.30 g., 6.83 mmole) was added and stirred over 1 hour. A saturated solution of sodium bicarbonate (20 mL) was added followed by water (250 mL). The acetone was evaporated leaving a tacky solid in water. This tacky solid was dissolved in ether and washed with water four times, dried (MgSO4), filtered and the solvent evaporated in vacuo to leave 96.91 g of crude methyl 3-(2-formylthiophen-3-yl)-3-thiapropionate (5) which was used in the next step without purification.

Workup

  1. additionwas added
  2. customThe acetone was evaporated
  3. customleaving a tacky solid in water
  4. washwashed with water four times
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-1e0c47b4ab974cadbe646106bc3ce904
Source dataset
uspto-grants-1989_10
Patent number
US04876271

Reaction notes

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