4-Toluenesulfonyl chloride → Cyclobutylmethyl 4-methylbenzenesulfonate
Reaction equation
[CH:1]1([CH2:5][OH:6])[CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH:1]1([CH2:5][O:6][S:13]([C:10]2[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=2)(=[O:15])=[O:14])[CH2:4][CH2:3][CH2:2]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of cyclobutanemethanol (4.0 g, 46.4 mmol) in dichloromethane (28 mL) at 25° C. was treated with 4-dimethylaminopyridine (6.23 g, 50.9 mmol). The reaction was then cooled to 0° C. and was treated with para-toluenesulfonylchloride (8.95 g, 46.94 mmol). The reaction was allowed to slowly warm to 25° C. and was allowed to stir overnight. After this time, the reaction was partitioned between water (200 mL) and methylene chloride (2×200 mL). The combined organics were washed with a 1N aqueous hydrochloric acid solution and a saturated aqueous sodium chloride solution (1×200 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford toluene-4-sulfonic acid cyclobutylmethyl ester (10.87 g, 97%) as colorless oil which was used without further purification.
Workup
- temperatureto slowly warm to 25° C.
- customAfter this time, the reaction was partitioned between water (200 mL) and methylene chloride (2×200 mL)
- washThe combined organics were washed with a 1N aqueous hydrochloric acid solution
- dry with materiala saturated aqueous sodium chloride solution (1×200 mL), dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b799e463ef0b4aa7a7eb501dcdb18601
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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