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

HRID 1095170Notes

Reaction equation

HRID 1095170 reaction equation
[CH2:1]([C:3]1([CH2:7][OH:8])[CH2:6][O:5][CH2:4]1)[CH3:2].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([C:3]1([CH2:7][O:8][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:9])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH2:6][O:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 76444Oxt-101

Product 1

HCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonateYield 70.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (3-ethyl-oxetan-3-yl)-methanol (11.6 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 (19 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-f3d281d411e34a3099e879b08dedd83f
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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