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

HRID 1880552

Reaction equation

HRID 1880552 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-e834f13a406a4731b6309dc76626008c
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Linked notes

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