Pyridine → HCID 86754222, compound

HRID 581888Notes

Reaction equation

HRID 581888 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH2:17][CH2:18][OH:19].N1C=CC=C[CH:21]=1>>[C:3]1([CH3:21])[C:4]([S:7]([O:19][CH2:18][CH2:17][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:12]2)(=[O:8])=[O:9])=[CH:5][CH:6]=[CH:1][CH:2]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 69833Cyclopentaneethanol

Product 1

HCID 86754222HCID 86754222, compoundYield 73%

Procedure

A para-toluenesulfonyl chloride (16.0 g, 83.8 mmol) was added to the pyridine (250 ml) solution of (2-cyclopentyl)ethyl alcohol (8.76 g, 76.2 mmol) and then the reaction mixture was stirred at room temperature for 6 hrs. After the removement of pyridine, the residue was extracted with ethyl acetate, washed with 1N HCl, dried, filtered and separated by column chromatography to give a desirable product (15.7 g).

Workup

  1. extractionAfter the removement of pyridine, the residue was extracted with ethyl acetate
  2. washwashed with 1N HCl
  3. customdried
  4. filtrationfiltered
  5. customseparated by column chromatography

Sources & evidence

ORD record
ord-d8a64a082bcd4550930524013e752466
Source dataset
uspto-grants-1999_07
Patent number
US05922727

Reaction notes

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