4-Toluenesulfonyl chloride → HCID 131725182, compound

HRID 723642Notes

Reaction equation

HRID 723642 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 131725182HCID 131725182, compoundYield 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-0d2c06d1412547b89eed8534ad717d46
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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