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

HRID 1387474Notes

Reaction equation

HRID 1387474 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 methlyene 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 methlyene chloride
  5. extractionThe methylene chloride extract
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a344be74b69c47508eb90778fa6a2031
Source dataset
uspto-grants-2001_07
Patent number
US06268392B1

Reaction notes

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