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

HRID 504457Notes

Reaction equation

HRID 504457 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-0e8cefc30b254489b0ee039b34623f5a
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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