Pyridine → HCID 13187521, compound

HRID 634711Notes

Reaction equation

HRID 634711 reaction equation
[CH:1]1([O:6][CH2:7][CH2:8][OH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10]1(C)[CH:15]=[CH:14][CH:13]=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:11]=1.N1C=CC=C[CH:22]=1>>[C:15]1([CH3:22])[CH:10]=[CH:11][C:12]([S:16]([O:9][CH2:8][CH2:7][O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:17])=[O:18])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 1049Pyridine2×HCID 27345953-Methylbenzenesulphonyl chlorideHCID 131875202-(Cyclopentyloxy)ethan-1-ol

Product 1

HCID 13187521HCID 13187521, compoundYield 73%

Procedure

2-Cyclopentyloxyethanol (4.3 g, 33.1 mmol) in pyridine (18 ml) was added dropwise to a solution of 3-toluenesulphonyl chloride (6.8 g, 35.7 mmol) in pyridine (27 ml) at 5° C. The mixture was allowed to warm to ambient temperature, and stirred overnight. The mixture was poured onto ice containing concentrated hydrochloric acid (46 ml) and the product was extracted with ether. The organic phase was washed with 2M hydrochloric acid, dried (MgSO4) and the solvent removed by evaporation to give 2-cyclopentyloxyethyl 4-toluenesulphonate (6.9 g, 73%) which was used without further purification.

Workup

  1. additionThe mixture was poured onto ice containing concentrated hydrochloric acid (46 ml)
  2. extractionthe product was extracted with ether
  3. washThe organic phase was washed with 2M hydrochloric acid
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-cd77fb3878904afc8634985bf4a3df0d
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

Loading…