Methanol → methyl 2H-thiopyran-3-carboxylate

HRID 1267675Notes

Reaction equation

HRID 1267675 reaction equation
[S:1]1[CH2:6][CH2:5][CH:4]=[C:3]([C:7]([O-:9])=[O:8])[CH2:2]1.[CH3:10]O>[Pd].C>[S:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 219460775,6-dihydro-2H-thiopyran-3-carboxylate

Product 1

HCID 21946080methyl 2H-thiopyran-3-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 14818447PalladiumcarbonCatalyst

Procedure

A solution of 832 mg (4.37 mmole) of 5,6-dihydro-2H-thiopyran-3-carboxylate, 1,1 dioxide from part D in methanol (40 mL) was hydrogenated in the presence of 400 mg (50% wt) of 10% Pd/charcoal for 4 hrs. at room temperature and 50 psig of H2. The catalyst was removed by vacuum filtration through a short plug of packed celite and the solvent removed in vacuo to give 802 mg (96%) of methyl 2H-thiopyran-3-carboxylate, 1,1-dioxide as a white solid; mass spectrum m/z=193 (CI,M+H)

Workup

  1. customat room temperature
  2. customThe catalyst was removed by vacuum filtration through a short plug of packed celite
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e83f7e369af344ed9677ae3ab0202bc0
Source dataset
uspto-grants-2003_04
Patent number
US06552203B2

Reaction notes

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