Triethylamine → (1-Phenylcyclopentyl)methyl methanesulfonate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[C:13]1([C:19]2([CH2:24][OH:25])[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([O:25][CH2:24][C:19]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1)(=[O:4])=[O:3]Participants
Procedure
659 mg (6.07 mmol) of methanesulfonyl chloride and then 838 μl (6.01 mmol) of triethylamine were added, whilst cooling in an ice-salt bath, to a solution of 1.00 g (5.67 mmol) of (1-phenylcyclopentyl)methanol [prepared as described in step (i) above] in 18 ml of methylene chloride, and the resulting mixture was stirred for 1 hour. At the end of this time, the reaction mixture was diluted with diethyl ether, and the diluted mixture was washed with 2N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off to give 1.44 g (a quantitative yield) of the title compound as colorless crystals.
Workup
- washthe diluted mixture was washed with 2N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
- dry with materialThe organic phase was dried over anhydrous sodium sulfate
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-011aacb0c6284a089459c224e0b4c6ce
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05534529
Reaction notes
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