p-Toluenesulfonic acid → 4,5-Dihydro-2-(trimethylsilyl)-7H-thieno[2,3-c]pyran-7-one
Reaction equation
O[CH2:2][CH2:3][C:4]1[CH:8]=[C:7]([Si:9]([CH3:12])([CH3:11])[CH3:10])[S:6][C:5]=1[C:13]([OH:15])=[O:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:12][Si:9]([CH3:10])([CH3:11])[C:7]1[S:6][C:5]2[C:13](=[O:14])[O:15][CH2:2][CH2:3][C:4]=2[CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
A mixture of 3-(2-Hydroxy-ethyl)-5-trimethylsilanyl-thiophene-2-carboxylic acid (4.1 g) and p-Toluenesulfonic acid (577.9 mg) in toluene (100 mL) was heated to 10° C. for 6 h. The solvent was removed in vacuum and the residue taken up in water and ethyl acetate. The aqueous phase was extracted with ethyl acetate three times. The combined organic phases were dried over sodium sulfate and the solvent was removed in vacuum. In this way the product was obtained with molecular weight 226.37 (C10H14O2SSi); MS (ESI): 227 (M+H+).
Workup
- customThe solvent was removed in vacuum
- extractionThe aqueous phase was extracted with ethyl acetate three times
- dry with materialThe combined organic phases were dried over sodium sulfate
- customthe solvent was removed in vacuum
- customIn this way the product was obtained with molecular weight 226.37 (C10H14O2SSi)
Sources & evidence
- ORD record
- ord-90e643e205454f2a8d495babb761a011
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822495B2
Reaction notes
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