4-Toluenesulfonyl chloride → 4H-Thieno[2,3-c]furan-6-one
Reaction equation
O[CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([OH:10])=[O:9].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[S:5]1[C:4]2[C:8](=[O:9])[O:10][CH2:2][C:3]=2[CH:7]=[CH:6]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-hydroxymethyl-thiophene-2-carboxylic acid (25 mg, 0.15 mmol) in dichloromethane (4 ml) and triethylamide (1.5 mL) is treated with p-toluenesulfonyl chloride (50 mg, 0.26 mmol) and the reaction mixture is stirred at room temperature overnight. The reaction mixture is concentrated and the product is purified by chromatography (silica gel, ethylacetate/hexane) to give the title compound. This material was used directly in the preparation of Example 70.
Workup
- concentrationThe reaction mixture is concentrated
- customthe product is purified by chromatography (silica gel, ethylacetate/hexane)
Sources & evidence
- ORD record
- ord-4656d918e5db44528d2643027bb0f2b0
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455535B2
Reaction notes
Loading…