Dichloromethane → 3-Chloromethyl-2-(2-p-toluenesulfonyloxyethyl) thiophene

HRID 270649Notes

Reaction equation

HRID 270649 reaction equation
O[CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][CH2:9][OH:10].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C.[Cl:29]CCl>>[Cl:29][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][CH2:9][O:10][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 111827612-(3-Hydroxymethylthiophen-2-yl)ethanol

Product 1

HCID 877814753-Chloromethyl-2-(2-p-toluenesulfonyloxyethyl) thiopheneYield 48%

Procedure

1.5 g of the compound obtained in Example 2 was dissolved in 40 mL of dichloromethane, and the resulting solution was cooled to below 5° C. To the solution, 3.6 g of p-toluenesulfonyl chloride and 1.9 g of triethylamine were added dropwise, and the resulting mixture was warmed to room temperature, stirred for 6 hours and washed twice with 20 ml portions of water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography (eluent, n-hexane:ethyl acetate=10:1) to obtain 1.5 g (yield of 48%) of the title compound as an oil.

Workup

  1. temperaturethe resulting solution was cooled to below 5° C
  2. washwashed twice with 20 ml portions of water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5fa56df660304325bf704ae2a179bba8
Source dataset
uspto-grants-2008_11
Patent number
US07449580B2

Reaction notes

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