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

HRID 1095167Notes

Reaction equation

HRID 1095167 reaction equation
[CH3:1][C:2]1([CH2:6][OH:7])[CH2:5][O:4][CH2:3]1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][C:2]1([CH2:6][O:7][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:8])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH2:5][O:4][CH2:3]1

Participants

5

Reactant 2

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

Product 1

HCID 5461213(3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonateYield 70.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (3-methyl-oxetan-3-yl)-methanol (10.2 g, 0.1 mol) and DMAP (18.3 g, 0.15 mol) in DCM (100 mL) was added 4-methyl-benzenesulfonyl chloride (19 g, 0.1 mol). The mixture was stirred at room temperature for 1 h, then filtered. The filtrate was washed with HCl aq. (1 M) and water, dried over anhydrous Na2SO4 and concentrated to give the title compound (18 g).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with HCl aq. (1 M) and water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-380058def3c14b9a83814d82cfc8dd12
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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