m-Chloroperbenzoic acid → HCID 20093198, compound

HRID 274346Notes

Reaction equation

HRID 274346 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][S:8][CH2:9][CH2:10][OH:11])[CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:17]>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][S:8]([CH2:9][CH2:10][OH:11])=[O:17])[CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20093199HCID 20093199, compound

Product 1

HCID 20093198HCID 20093198, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred solution of 2-(3-pyridylmethylthio)ethanol (3.38 g, 20 mmol) in dichloromethane (50 ml) at 0° C. was treated dropwise with a solution of m-chloroperoxybenzoic acid in dichloromethane (50 ml). The mixture was stirred at 0° C. for 1 hr and at room temperature for 3 hrs. The mixture was evaporated in vacuo and purified by flash chromatography on silica eluting with 20% methanol in ethyl acetate to give 2-(3-pyridylmethylsulphinyl)ethanol (3.5 g), as colourless crystals, m.p. 84°-86° C.;

Workup

  1. customThe mixture was evaporated in vacuo
  2. custompurified by flash chromatography on silica eluting with 20% methanol in ethyl acetate

Sources & evidence

ORD record
ord-59a794b44ef1478aa26769b26cc86d32
Source dataset
uspto-grants-1995_02
Patent number
US05389649

Reaction notes

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