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

HRID 1837643Notes

Reaction equation

HRID 1837643 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-89b07a1f69dd4e5aada40e777e2c9082
Source dataset
uspto-grants-2004_08
Patent number
US06784201B2

Reaction notes

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