Triethylamine → HCID 16070660, compound

HRID 888312Notes

Reaction equation

HRID 888312 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 3-ethyl-3-hydroxymethyloxetane (465 g (4.0 mol)), triethylamine (486 g (4.8 mol)) and toluene (1,840 ml) to a glass flask having an inner volume of 5,000 ml equipped with a stirrer, a thermometer and a dropping funnel, while keeping the liquid temperature at 5-10° C., methanesulfonyl chloride (504 g (4.4 mol)) was gradually added to react at the same temperature for 3 hours and at room temperature for 3 hours with stirring. After the completion of the reaction, an aqueous saturated sodium bicarbonate solution (930 ml) was added to the reaction solution and a liquid separation was performed. Subsequently an aqueous layer was extracted with toluene (930 ml), an extract was combined with a previously extracted organic layer, and the combined liquid was washed with water (465 ml). A resultant organic layer was concentrated under reduced pressure to give, as a brown liquid, 3-ethyl-3-methanesulfonyloxymethyloxetane (777 g) having a purity of 95% (a value measured by 1H-NMR) (an isolated yield based on 3-ethyl-3-hydroxymethyloxetane: 95%).

Workup

  1. customequipped with a stirrer
  2. customat 5-10° C.
  3. customto react at the same temperature for 3 hours and at room temperature for 3 hours
  4. customAfter the completion of the reaction
  5. customa liquid separation
  6. extractionSubsequently an aqueous layer was extracted with toluene (930 ml)
  7. washthe combined liquid was washed with water (465 ml)
  8. concentrationA resultant organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f0a35fbc2e95419ca5f0206cac714e8c
Source dataset
uspto-grants-2012_08
Patent number
US08247583B2

Reaction notes

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