Triethylamine → HCID 22930225, compound

HRID 968807Notes

Reaction equation

HRID 968807 reaction equation
C(N(CC)CC)C.[CH2:8]([CH:10]([CH2:14][CH3:15])[CH2:11][CH2:12][OH:13])[CH3:9].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl.C(OCC)C>[CH3:16][S:17]([O:13][CH2:12][CH2:11][CH:10]([CH2:14][CH3:15])[CH2:8][CH3:9])(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6410053-ethylpentan-1-ol

Product 1

HCID 22930225HCID 22930225, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.4 ml, 17 mmol) was added dropwise to a solution of the 3-ethyl-1-pentanol (1.0 g, 8.6 mmol) and methanesulfonyl chloride (0.8 ml, 10 mmol) in dichloromethane (20 ml) while cooling on ice, and the mixture was stirred for 2 hours. After diluting the reaction mixture with diethyl ether, it was washed with water and brine, and the organic layer was dried over anhydrous sodium sulfate prior to distillation under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.38 g) as a colorless oil.

Workup

  1. temperaturewhile cooling on ice
  2. washwas washed with water and brine
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. distillationto distillation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cbd34d5240dd442c901ffcc5fef19971
Source dataset
uspto-grants-2007_12
Patent number
US07304083B2

Reaction notes

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