Triethylamine → 3-Mesyloxy-2-methoxy-1-hexen-5-yne

HRID 4289Notes

Reaction equation

HRID 4289 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[OH:6][CH:7]([CH2:12][C:13]#[CH:14])[C:8]([O:10][CH3:11])=[CH2:9].C(N(CC)CC)C>C(Cl)Cl>[S:1]([O:6][CH:7]([CH2:12][C:13]#[CH:14])[C:8]([O:10][CH3:11])=[CH2:9])([CH3:4])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 201523313-Hydroxy-2-methoxy-1-hexen-5-yne

Product 1

HCID 201523303-Mesyloxy-2-methoxy-1-hexen-5-yne

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mesyl chloride (1.73 ml) was added dropwise to a solution of 3-hydroxy-2-methoxy-1-hexen-5-yne (2 g) and triethylamine (3.32 ml) in methylene chloride (20 ml) under ice-cooling over a period of 10 minutes. After being stirred for 48 hours at room temperature the mixture was washed successively with water, aqueous sodium bicarbonate solution, and brine, dried over magnesium sulfate, and evaporated in vacuo to give 3-mesyloxy-2-methoxy-1-hexen-5-yne (3.45 g).

Workup

  1. temperaturecooling over a period of 10 minutes
  2. washwas washed successively with water, aqueous sodium bicarbonate solution, and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-fb1b8a9a3abb43df9bafa1d48884824e
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Reaction notes

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