Ethyl Methanesulfonate → Ethyl 2-(5-chloro-2-thienyl)-2-hydroxy-1-propanesulfonate
Reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH3:7])(=[O:4])=[O:3].[C:8]([C:11]1[S:12][C:13]([Cl:16])=[CH:14][CH:15]=1)(=[O:10])[CH3:9]>C1COCC1>[Cl:16][C:13]1[S:12][C:11]([C:8]([OH:10])([CH3:9])[CH2:1][S:2]([O:5][CH2:6][CH3:7])(=[O:4])=[O:3])=[CH:15][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of ethyl methanesulphonate (4.97 g) in THF (20 ml) was added dropwise to a solution of lithium hexamethyldisilylamide (42.0 ml of 1M solution in THF plus 20 ml of THF) at −78° C. under nitrogen, and the solution was stirred for 30 min. A solution of 2-acetyl-5-chlorothiophene (6.75 g) in THF (70 ml) was added to this over 15 min and the temperature maintained at −78° C. for 90 min. The reaction was quenched with saturated aqueous ammonium chloride and the mixture extracted with ethyl acetate. The combined organic fractions were washed with brine; dried (over magnesium sulphate) and concentrated under reduced pressure to afford a crude oil that was purified by Biotage™ chromatography (silica, eluting with ether-cyclohexane 1:3) to give the title compound (10.9 g) as a colourless oil.
Workup
- customThe reaction was quenched with saturated aqueous ammonium chloride
- extractionthe mixture extracted with ethyl acetate
- washThe combined organic fractions were washed with brine
- dry with materialdried (over magnesium sulphate)
- concentrationconcentrated under reduced pressure
- customto afford a crude oil that
- customwas purified by Biotage™ chromatography (silica, eluting with ether-cyclohexane 1:3)
Sources & evidence
- ORD record
- ord-7961ed9bb7f74f8c8c7b17fef4af0e9f
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482374B2
Reaction notes
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