Triethylamine → HCID 86624770, compound
Reaction equation
[CH3:1][C:2]1([OH:9])[CH2:4][CH:3]1[Si:5]([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][C:2]1([O:9][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:4][CH:3]1[Si:5]([CH3:8])([CH3:7])[CH3:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
16 g (0.11 mole) of a trans isomer, a cis isomer or a trans/cis isomer mixture of 1-methyl-1-hydroxy-2-(trimethylsilyl)cyclopropane, prepared in Section (1) was dissolved in 150 ml of dichloromethane and 25 ml of triethylamine was added thereto. The reaction solution was cooled to 0° C., 16 g (0.14 mole) of methanesulfonylchloride was gradually added thereto and the mixture was vigorously stirred for 1 hour. 50 mL of a saturated aqueous NaHCO3 solution was added to the reaction mixture to complete the reaction. An organic layer was separated from the reaction solution, dried over anhydrous magnesium sulfate (MgSO4), and concentrated by distillation of the solvent. Although the concentrate may be used directly without any further purification, it was finely purified by vacuum distillation (55-60° C./0.1 mmHg). As a result, 21.4 g (0.0096 mole, yield: 87%) of 1-methyl-1-(methanesulfonyloxy)-2-(trimethylsilyl)cyclopropane was obtained as a trans isomer, a cis isomer and a mixture thereof.
Workup
- customthe reaction
- customAn organic layer was separated from the reaction solution
- dry with materialdried over anhydrous magnesium sulfate (MgSO4)
- concentrationconcentrated by distillation of the solvent
- concentrationAlthough the concentrate may
- custombe used directly without any further purification, it
- distillationwas finely purified by vacuum distillation (55-60° C./0.1 mmHg)
Sources & evidence
- ORD record
- ord-18037ca4d3384e06bcf67040e2dfc67b
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314051B2
Reaction notes
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