Pyridine → Tert-butyl 3-mesyloxycyclopentanoate

HRID 1681076Notes

Reaction equation

HRID 1681076 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[OH:6][CH:7]1[CH2:11][CH2:10][CH:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1.N1C=CC=CC=1>C(Cl)Cl>[S:1]([O:6][CH:7]1[CH2:11][CH2:10][CH:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1)([CH3:4])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 14009988tert-Butyl 3-hydroxycyclopentanecarboxylate

Product 1

HCID 14009993Tert-butyl 3-mesyloxycyclopentanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mesyl chloride (0.15 ml) was added dropwise to tert-butyl 3-hydroxycyclopentanoate (373 mg) dissolved in methylene chloride (2 ml) and pyridine (0.32 ml) at a temperature of 0° C. The mixture was stirred at a room temperature for 4 hours. The reaction mixture was poured into ice-water (10 ml). The mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then evaporated to obtained the title compound having the following physical data.

Workup

  1. customat a temperature of 0° C
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-10909c6c3a334baa8e2a6fe8088af15c
Source dataset
uspto-grants-1992_12
Patent number
US05168101

Reaction notes

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