Triethylamine → HCID 86624771, compound

HRID 1695080Notes

Reaction equation

HRID 1695080 reaction equation
[CH2:1]([C:3]1([OH:10])[CH2:5][CH:4]1[Si:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].C(N(CC)CC)C.[CH2:18]([S:20](Cl)(=[O:22])=[O:21])[CH3:19].C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([C:3]1([O:10][S:20]([CH2:18][CH3:19])(=[O:22])=[O:21])[CH2:5][CH:4]1[Si:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 67276772HCID 67276772, compound2×

Product 1

HCID 86624771HCID 86624771, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.5 g of 1-ethyl-1-hydroxy-2-(trimethylsilyl)cyclopropane prepared in Section (1) was dissolved in 15 mL of dichloromethane, and 2.3 g of triethylamine was added to the resulting solution. The reaction solution thus prepared was cooled to 0° C., 1.8 g of ethanesulfonylchloride 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 solution, thereby terminating the reaction. An organic layer was separated from the reaction solution, dried over anhydrous magnesium sulfate (MgSO4), and concentrated by solvent distillation at a low temperature of less than 30° C. Although it may be used directly without any further treatment, the resulting concentrate was purified by silica gel chromatography using hexane and ethyl acetate to obtain 1.62 g of 1-ethyl-1-(ethanesulfonyloxy)-2-(trimethylsilyl)cyclopropane as a pure trans isomer. Results of 1H-NMR and 13C-NMR for the trans isomer are given below.

Workup

  1. customThe reaction solution thus prepared
  2. customterminating
  3. customthe reaction
  4. customAn organic layer was separated from the reaction solution
  5. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  6. concentrationconcentrated by solvent distillation at a low temperature of less than 30° C
  7. concentrationthe resulting concentrate
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-9d7d5600aab148318ac1349a8662a0c9
Source dataset
uspto-grants-2012_04
Patent number
US08163244B2

Reaction notes

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