4-Toluenesulfonyl chloride → 25745-01-1

HRID 1254149Notes

Reaction equation

HRID 1254149 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]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 200942743-(Hydroxymethyl)-2-thiophenecarboxylic acid

Product 1

HCID 2239891125745-01-1

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. concentrationThe reaction mixture is concentrated
  2. 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

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