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

HRID 478881Notes

Reaction equation

HRID 478881 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-9d8f86e80095481784dd189bdd722cb9
Source dataset
uspto-grants-2003_11
Patent number
US06642268B2

Reaction notes

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