4-Toluenesulfonyl chloride → 5-Methyl-2-furanethanol 4-methylbenzenesulfonate

HRID 2110402Notes

Reaction equation

HRID 2110402 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][C:13]1[O:17][C:16]([CH2:18][CH2:19][OH:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[CH3:12][C:13]1[O:17][C:16]([CH2:18][CH2:19][OH:20])=[CH:15][CH:14]=1.[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:10])(=[O:17])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 110623902-(5-Methylfuran-2-yl)ethan-1-ol

Product 1

HCID 1317251825-Methyl-2-furanethanol 4-methylbenzenesulfonateYield 152.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Methylbenzenesulfonyl chloride (907 mg, 4.76 mmol) was added to a solution of compound 21A (500 mg, 3.96 mmol) in 6 mL of dry pyridine. The reaction was stirred at room temperature for 4 h and then quenched with ice. The reaction mixture was extracted with CH2Cl2 and the combined organic layers were washed with saturated aqueous sodium bicarbonate and water, dried and concentrated under reduced pressure to give 900 mg (81%) of compound 24A as a yellow oil.

Workup

  1. customquenched with ice
  2. extractionThe reaction mixture was extracted with CH2Cl2
  3. washthe combined organic layers were washed with saturated aqueous sodium bicarbonate and water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52fac033d2e24aeb93f2f4b8c57d6b41
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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