Methanesulfonyl chloride → HCID 131730066, compound

HRID 1877748Notes

Reaction equation

HRID 1877748 reaction equation
[CH3:1][C:2]1([OH:9])[CH2:4][CH:3]1[Si:5](C)(C)[CH3:6].[CH3:10][C:11]1(O)[CH2:13][CH:12]1[Si](C)(C)CC.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C([O-])(O)=O.[Na+]>ClCCl.C(N(CC)CC)C>[CH3:1][C:2]1([O:9][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:4][CH:3]1[SiH2:5][CH2:6][C:11]([CH3:13])([CH3:12])[CH3:10]

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 13407681HCID 13407681, compoundHCID 46899441HCID 46899441, compound

Product 1

HCID 131730066HCID 131730066, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

1.6 g (0.010 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 15 ml of dichloromethane and 23 g of triethylamine was added thereto. The reaction solution was cooled to 0° C., 1.3 g (0.011 mole) of methanesulfonyl chloride was gradually added thereto and the mixture was vigorously stirred for 1 hour. 5 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 at a low temperature of 30° C. or less. Although the concentrate may be used directly without any further purification, it was purified over silica gel again to obtain 1.74 g (7.3 mmole, yield: 74%) of 1-methyl-1-(methanesulfonyloxy)-2-(trimethylethylsilyl)cyclopropane.

Workup

  1. customthe reaction
  2. customAn organic layer was separated from the reaction solution
  3. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  4. concentrationconcentrated by distillation of the solvent at a low temperature of 30° C. or less
  5. concentrationAlthough the concentrate may
  6. custombe used directly without any further purification, it
  7. customwas purified over silica gel again

Sources & evidence

ORD record
ord-4555625860b94954a7923b5ac1b5bfa0
Source dataset
uspto-grants-2012_11
Patent number
US08314051B2

Reaction notes

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