4-Toluenesulfonyl chloride → (3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

HRID 2194549Notes

Reaction equation

HRID 2194549 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=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:18][CH2:17][C:13]2([CH3:12])[CH2:16][O:15][CH2:14]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of p-toluenesulfonyl chloride (14.3 g, 75 mmol) in pyridine (60 mL) is slowly added 3-methyl-3-oxetanemethanol A3a (5.1 g, 50 mmol) over 10 min. The resulting suspension is stirred at rt for 1.5 h and poured into vigorously stirred ice water (300 mL). The slurry is stirred for 45 min. The solid is collected by filtration, washed with ice-cold H2O (100 mL), and dried under high vacuum to afford (3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate A3b as a white powder. The compound is used in the next step without further purification. 1H-NMR (400 MHz, CDCl3) δ=7.83 (d, J=8.4 Hz, 2H), 7.39 (d, J=8.4 Hz, 2H), 4.39 (d, J=6.4 Hz, 2H), 4.36 (d, J=6.4 Hz, 2H), 4.13 (s, 2H), 2.49 (s, 3H), 1.33 (s, 3H).

Workup

  1. customover 10 min
  2. stirringThe slurry is stirred for 45 min
  3. filtrationThe solid is collected by filtration
  4. washwashed with ice-cold H2O (100 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-1f8c98190cf34cdd82d0f1763e2de825
Source dataset
uspto-grants-2012_12
Patent number
US08334288B2

Reaction notes

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