4-Toluenesulfonyl chloride → HCID 19849036, compound

HRID 1608274Notes

Reaction equation

HRID 1608274 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]2([CH2:11][CH2:10][CH:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8]2)[O:4]1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1.CCOCC>[CH3:28][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:1][CH2:2][CH:3]2[CH2:7][O:6][C:5]3([CH2:11][CH2:10][CH:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8]3)[O:4]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 19849039HCID 19849039, compound

Product 1

HCID 19849036HCID 19849036, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

To a cold (00) stirred solution of the alcohol of Example K (2.44 g, 10 mmol) in pyridine (30 ml) is added p-toluenesulfonyl chloride (1.91 g, 10 mmol) in portions over 15 minutes. When addition is completed, the reaction mixture is stirred at room temperature for 2 hrs. The reaction mixture is diluted with ether and washed successively with water, 0.5N aqueous sodium bisulfate solution, 5% aqueous sodium bicarbonate solution and water. The organic layer is dried over sodium sulfate, filtered, and the filtrate is concentrated on the rotary evaporator to give the titled compound.

Workup

  1. additionWhen addition
  2. washwashed successively with water, 0.5N aqueous sodium bisulfate solution, 5% aqueous sodium bicarbonate solution and water
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated on the rotary evaporator

Sources & evidence

ORD record
ord-18cc650e5e4547fbbb374dd04afcef82
Source dataset
uspto-grants-1989_09
Patent number
US04870098

Reaction notes

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