Triethylamine → HCID 86624770, compound

HRID 1695079Notes

Reaction equation

HRID 1695079 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

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 13407681HCID 13407681, compound

Product 1

HCID 86624770HCID 86624770, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.2 g of a trans and cis mixture of 1-methyl-1-hydroxy-2-(trimethylsilyl)cyclopropane, prepared in Section 1, was dissolved in 15 mL of dichloromethane, and 1.7 g of triethylamine was added to the resulting solution. The reaction mixture was cooled to 0° C., 1.8 g of methanesulfonylchloride was gradually added thereto and the mixture was vigorously stirred for 1 hour. 5 mL of a saturated NaHCO3 solution was added to the reaction mixture, thereby terminating the reaction. An organic layer was separated, dried over anhydrous magnesium sulfate (MgSO4), and concentrated by low vacuum distillation at a low temperature of less than 30° C. Although it may be used directly without any further purification, the concentrate was finely purified by vacuum distillation (65-70° C./0.1 mmHg). As a result, 2.8 g of 1-methyl-1-(methanesulfonyloxy)-2-(trimethylsilyl)cyclopropane was obtained as a mixture of cis and trans isomers in a ratio of 3 to 4:1. Results of 1H-NMR and 13C-NMR for the major isomer (trans isomer) of the mixture are given below.

Workup

  1. customprepared in Section 1
  2. customterminating
  3. customthe reaction
  4. customAn organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  6. concentrationconcentrated by low vacuum distillation at a low temperature of less than 30° C
  7. customAlthough it may be used directly without any further purification
  8. distillationthe concentrate was finely purified by vacuum distillation (65-70° C./0.1 mmHg)

Sources & evidence

ORD record
ord-feeec5a2c6b747cbad3bb7aaab81d146
Source dataset
uspto-grants-2012_04
Patent number
US08163244B2

Reaction notes

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