4-Toluenesulfonyl chloride → HCID 56624501, compound

HRID 638630Notes

Reaction equation

HRID 638630 reaction equation
[CH2:1]([C@H:5]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6]1)[CH2:2][CH2:3][CH3:4].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH2:1]([C@H:5]1[CH2:9][CH2:8][CH:7]([O:10][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 56621620HCID 56621620, compound

Product 1

HCID 56624501HCID 56624501, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution cooled with ice, of 94 mg of (1RS,3S)-3-butylcyclopentan-1-ol (prepared in Reference Example 11) in 2 ml of pyridine, 260 mg of p-toluenesulphonyl chloride was added, and the mixture was stirred for 30 min. at the same temperature and for 5 hrs at room temperature. The reaction solution was poured into ice-water. The mixture was extracted with a mixture of pentane and diethyl ether (1:1). The extract was washed with water, dried over magnesium sulphate, and concentrated under ambient pressure at 50° C. to give 190 mg of the title compound having the following physical characteristic.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with a mixture of pentane and diethyl ether (1:1)
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under ambient pressure at 50° C.

Sources & evidence

ORD record
ord-78fc0e1b0d904e5587a4f7497e6f2b1f
Source dataset
uspto-grants-1985_12
Patent number
US04562207

Reaction notes

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