Pyridine → (3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonate

HRID 746346Notes

Reaction equation

HRID 746346 reaction equation
[CH2:1]([C:3]1([CH2:7][OH:8])[CH2:6][O:5][CH2:4]1)[CH3:2].N1C=CC=CC=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>O>[S:21]([O:8][CH2:7][C:3]1([CH2:1][CH3:2])[CH2:6][O:5][CH2:4]1)([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 76444Oxt-101

Product 1

HCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3-ethyl-3-hydroxymethyloxetane (trade name of product, OXT-101®, manufactured by To a Gosei Co.; 116 g) was added to pyridine (500 mL) and cooled to 0° C. while stirring. p-Toluene sulfonyl chloride (190 g) was added divisionally for several times. After stirring for 5 hours while keeping at 0° C., the reaction mixture was poured to iced water (1 L). It was extracted with diethyl ether (500 mL), the pH was rendered acidic with 3% hydrochloric acid, and extracts were washed with water. Then, the extracts were washed with a saturated solution of sodium carbonate and water successively and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 3-[(tosyloxy)methyl]3-ethyloxetane (243 g).

Workup

  1. stirringAfter stirring for 5 hours
  2. customwhile keeping at 0° C.
  3. extractionIt was extracted with diethyl ether (500 mL)
  4. washwere washed with water
  5. washThen, the extracts were washed with a saturated solution of sodium carbonate and water successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-25db0730452943b98863a06bede34555
Source dataset
uspto-grants-2008_07
Patent number
US07393569B2

Reaction notes

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