Pyridine → (3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

HRID 907613Notes

Reaction equation

HRID 907613 reaction equation
[CH3:1][C:2]1([CH2:6][OH:7])[CH2:5][O:4][CH2:3]1.[C:8]1(C)[C:9]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=1.N1C=CC=C[CH:20]=1>>[CH3:1][C:2]1([CH2:6][O:7][S:14]([C:9]2[CH:8]=[CH:13][C:12]([CH3:20])=[CH:11][CH:10]=2)(=[O:15])=[O:16])[CH2:5][O:4][CH2:3]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 1378373-Methyl-3-oxetanemethanol

Product 1

HCID 5461213(3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Procedure

(3-Methyloxetan-3-yl)methanol (20 g, 190 mmol) was added to a solution of toluene sulfonylchloride (54.3 g, 285 mmol) in dry pyridine (100 ml) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was poured into crushed ice and stirred vigorously for 30 min. The precipitates were filtered and dried to give toluene-4-sulfonic acid 3-methyl-oxetan-3-ylmethyl ester (37 g) as a white powder.

Workup

  1. additionThe reaction mixture was poured
  2. custominto crushed ice
  3. stirringstirred vigorously for 30 min
  4. filtrationThe precipitates were filtered
  5. customdried

Sources & evidence

ORD record
ord-e81d810f279f486bb1a54e1b46351c23
Source dataset
uspto-grants-2011_09
Patent number
US08013186B2

Reaction notes

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