Triethylamine → HCID 16070660, compound

HRID 2066352Notes

Reaction equation

HRID 2066352 reaction equation
[CH2:1]([C:3]1([CH2:7][OH:8])[CH2:6][O:5][CH2:4]1)[CH3:2].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1([CH2:7][O:8][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:6][O:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 76444Oxt-101HCID 516892Sodium Bicarbonate

Product 1

HCID 16070660HCID 16070660, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After adding 465 g (4.0 mol) of 3-ethyl-3-hydroxymethyloxetane, 486 g (4.8 mol) of triethylamine, and 1840 ml of toluene in a glass flask having an internal volume of 5000 ml equipped with a stirrer, a thermometer, and a dropping funnel, 504 g (4.4 mol) of methanesulfonyl chloride was gently added while keeping the liquid temperature from 5° C. to 10° C. to carry out a reaction, while stirring, at the same temperature range for three hours and at room temperature for three hours. After completing the reaction, 930 ml of a saturated aqueous sodium hydrogen carbonate solution (concentration of 9.3 mass %) was added to the reaction solution to separate into a water layer and an organic layer. Then, after extracting the water layer with 930 ml of toluene, the extract was combined with the previous organic layer and washed with 465 ml of water. By concentrating the organic layer thus obtained under reduced pressure, 777 g of 3-ethyl-3-methanesulfonyloxymethyloxetane with a purity of 95 mass % (quantitative value determined by 1H-NMR) as a brown liquid was obtained (isolated yield based on 3-ethyl-3-hydroxymethyloxetane=95%).

Workup

  1. customequipped with a stirrer
  2. customfrom 5° C. to 10° C.
  3. customa reaction
  4. additionwas added to the reaction solution
  5. customto separate into a water layer
  6. extractionThen, after extracting the water layer with 930 ml of toluene
  7. washwashed with 465 ml of water
  8. concentrationBy concentrating the organic layer

Sources & evidence

ORD record
ord-6fe8260796f2475eb383089dd78982d5
Source dataset
uspto-grants-2012_10
Patent number
US08293448B2

Reaction notes

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