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

HRID 2217107Notes

Reaction equation

HRID 2217107 reaction equation
[CH2:1]([C:3]1([CH2:7][OH:8])[CH2:6][O:5][CH2:4]1)[CH3:2].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[S:15]([O:8][CH2:7][C:3]1([CH2:1][CH3:2])[CH2:6][O:5][CH2:4]1)([C:12]1[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=1)(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 76444Oxt-101

Product 1

HCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonateYield 90.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

116 g of 3-ethyl-3-hydroxymethyloxetane (Toa Gosei's trade name, OXT-101) was added to 500 ml of pyridine, and cooled to 0° C. with stirring. 190 g of p-toluenesulfonyl chloride divided into a few portions was added to it intermittently. Kept at 0° C., this was stirred for 5 hours, and then 1 L of ice-water was poured into the reaction mixture. This was extracted with 500 ml of diethyl ether. The diethyl ether layer was washed with 3% hydrochloric acid until its pH became acidic, and then washed with saturated sodium carbonate solution and water in this order, and thereafter dried with anhydrous magnesium sulfate. The solvent was evaporated away, and 243 g of 3-[(tosyloxy)methyl]-3-ethyloxetane was obtained.

Workup

  1. additionwas added to it intermittently
  2. stirringKept at 0° C., this was stirred for 5 hours
  3. extractionThis was extracted with 500 ml of diethyl ether
  4. washThe diethyl ether layer was washed with 3% hydrochloric acid until its pH
  5. washwashed with saturated sodium carbonate solution and water in this order
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated away

Sources & evidence

ORD record
ord-c5855366ef4942c58f3f209297b6ba40
Source dataset
uspto-grants-2008_08
Patent number
US07407691B2

Reaction notes

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