4-Toluenesulfonyl chloride → 2-(Furan-2-yl)ethyl 4-methylbenzene-1-sulfonate

HRID 1910780Notes

Reaction equation

HRID 1910780 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][OH:8].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1.C(Cl)(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][O:8][S:15]([C:12]1[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=1)(=[O:17])=[O:16]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 6421102-Furanethanol

Product 1

HCID 103331462-(Furan-2-yl)ethyl 4-methylbenzene-1-sulfonateYield 53.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-furan-2-yl-ethanol (1.6 g, 14.0 mmol) in a mixture of pyridine (5 mL) and chloroform (15 mL) was added para-toluenesulfonyl chloride (5.5 g, 28.0 mmol) and heated at 60° C. for 3 hrs. The reaction was cooled and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water, sat. sodium bicarbonate solution and dried over anhydrous sodium sulfate. The filtrate was concentrated, and the crude compound purified by column chromatography over silica gel (60-120 mesh) using 10% ethyl acetate/petroleum ether as eluent to afford toluene-4-sulfonic acid 2-furan-2-yl-ethyl ester (2.0 g, 32%) as an oil.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water, sat. sodium bicarbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe filtrate was concentrated
  7. customthe crude compound purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-2e4e4471185848f5b6ea1815a183596a
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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