Triethylamine → 2-Ethyl-2-(mesyloxymethyl)hexanal

HRID 1582999Notes

Reaction equation

HRID 1582999 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[CH2:13]([C:15]([CH2:22][OH:23])([CH2:18][CH2:19][CH2:20][CH3:21])[CH:16]=[O:17])[CH3:14]>>[CH2:13]([C:15]([CH2:22][O:23][S:2]([CH3:1])(=[O:4])=[O:3])([CH2:18][CH2:19][CH2:20][CH3:21])[CH:16]=[O:17])[CH3:14]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 125384672-Ethyl 2-(hydroxymethyl)hexanal

Product 1

HCID 115722172-Ethyl-2-(mesyloxymethyl)hexanalYield 103.4%

Procedure

To a cold (10° C.) solution of 12.6 g (0.11 mole) of methanesulfonyl chloride and 10.3 g (0.13 mole) of triethylamine was added dropwise 15.8 g of 2-ethyl-2-(hydroxymethyl)hexanal, prepared according to the procedure described in Chem. Ber. 98, 728-734 (1965), while maintaining the reaction temperature below 30° C. The reaction mixture was stirred at room temperature for 18 h, quenched with dilute HCl and extracted with methylene chloride. The methylene chloride extract was dried over MgSO4 and concentrated in vacuo to give 24.4 g of brown oil.

Workup

  1. customprepared
  2. temperature98, 728-734 (1965), while maintaining the reaction temperature below 30° C
  3. customquenched with dilute HCl
  4. extractionextracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3da9e9e60484d7799a7741d355c8a43
Source dataset
uspto-grants-2004_05
Patent number
US06740663B2

Reaction notes

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