Pyridine → 3-Methyl-3-(toluenesulfonyl-oxymethyl)oxetane

HRID 2223569

Reaction equation

HRID 2223569 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][C:13]1([CH2:17][OH:18])[CH2:16][O:15][CH2:14]1.N1C=CC=C[CH:20]=1>>[CH3:12][C:13]1([CH2:17][O:18][S:7]([C:4]2[C:5]([CH3:20])=[CH:6][CH:1]=[CH:2][CH:3]=2)(=[O:8])=[O:9])[CH2:16][O:15][CH2:14]1.[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)([OH:15])(=[O:9])=[O:8].[O:15]1[CH2:16][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 1378373-Methyl-3-oxetanemethanol

Product 2

HCID 534258303-Methyl-3-(toluenesulfonyl-oxymethyl)oxetaneHCID 86590555Oxetane tosylate

Procedure

p-Toluenesulfonyl chloride (57.2 g, 300 mmol) was dissolved in dry pyridine (400 mL) under nitrogen atmosphere. 3-methyl-3-(hydroxymethyl)oxetane (20.4 g, 200 mmol) was added slowly, and the solution was stirred for 1.5 h. Crushed ice (400 g) was then added to vigorously stirring mixture, which was allowed to stir for an additional 0.5 h. The white precipitate was then collected on Whatman filter paper #1 and washed with cold water. The product was dried under high vacuum to obtain 3-methyl-3-(toluenesulfonyl-oxymethyl)oxetane (oxetane tosylate) as a white powder of oxetane tosylate.

Workup

  1. stirringto vigorously stirring mixture, which
  2. stirringto stir for an additional 0.5 h
  3. customThe white precipitate was then collected on Whatman
  4. filtrationfilter paper #1
  5. washwashed with cold water
  6. customThe product was dried under high vacuum

Sources & evidence

ORD record
ord-24ae5ec1c8e94024b05495e038eb456f
Source dataset
uspto-grants-2008_05
Patent number
US07375134B2

Linked notes

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