Methanesulfonyl chloride → Ethyl 2-(methylsulfonyloxy)-2-(thiophen-2-yl)acetate
Reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH:5]([OH:11])[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[CH3:2].CCN(C(C)C)C(C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:11][CH:5]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:12])(=[O:25])=[O:24]Participants
Conditions
- Temperature
- 0 °C
Procedure
Hydroxy-thiophen-2-yl-acetic acid ethyl ester (4.58 g, 24.6 mmol) is dissolved in dry DCM (125 mL) and cooled at 0° C. DIPEA (5.15 mL, 29.5 mmol) and methanesulphonyl chloride (2.11 mL, 27.1 mmol) are added and the resulting solution is stirred at RT for 1 hour. DIPEA (0.859 ml, 4.92 mmol) and methanesulphonyl chloride (0.19 mL, 2.46 mmol) are added again. After being stirred at room temperature for 1 additional hour, a third portion of DIPEA (0.43 mL, 2.46 mmol) and methanesulphonyl chloride (77 ul, 0.98 mmol) is added. After 1 hour the reaction is completed. The mixture is diluted with DCM, washed with sat. NaHCO3, water and brine, dried (Na2SO4), filtered and evaporated. The resulting yellow oil is used in the next step without any further purification.
Workup
- stirringAfter being stirred at room temperature for 1 additional hour
- waitAfter 1 hour the reaction is completed
- washwashed with sat. NaHCO3, water and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
- customThe resulting yellow oil is used in the next step without any further purification
Sources & evidence
- ORD record
- ord-c412baf9c9634e81a981103a7f0ffa3d
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455646B2
Reaction notes
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