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

HRID 1259409Notes

Reaction equation

HRID 1259409 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.C(OCC)(=O)C>N1C=CC=CC=1.CCCCCC>[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

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 1378373-Methyl-3-oxetanemethanol

Product 1

HCID 5461213(3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonateYield 50%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

p-Toluene sulfonyl chloride (5.6 g, 29.41 mmol) was added to a cooled solution of (3-methyloxetan-3-yl)methanol (2 g, 19.60 mmol) in pyridine (25 mL) at 0° C. and the resulting reaction mass was stirred at 0° C. for 2 hours. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mass was poured into ice-water, stirred for 30 minutes, the solid formed was collected by filtration, washed with water and dried under reduced pressure to afford 2.5 g of the product (50% yield).

Workup

  1. customthe resulting reaction mass
  2. stirringstirred for 30 minutes
  3. customthe solid formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-813af315eb934ddb8c4dd445f9bea5f6
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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