Methanol → Ethyl [(prop-2-yn-1-yl)oxy]acetate

HRID 1153970Notes

Reaction equation

HRID 1153970 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[C:4]#[CH:5].Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].CO>C(OCC)C>[CH2:3]([O:6][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]#[CH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 7748Ethyl bromoacetateHCID 7859Propargyl alcoholHCID 24758Sodium hydride2×

Product 1

HCID 12883734Ethyl [(prop-2-yn-1-yl)oxy]acetateYield 70.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an anhydrous solution containing 5.1 g of 55% oily sodium hydride in 120 ml of diethyl ether were added 24 ml of an anhydrous diethyl ether solution containing 5.6 g of propargyl alcohol. The mixture was stirred at room temperature for 1.5 hours, after which 20.9 g of ethyl bromoacetate were added dropwise. The mixture was allowed to stand overnight, after which the excess sodium hydride was decomposed with methanol. After separating off the precipitate produced, the filtrate was distilled to give 10 g of ethyl α-propargyloxyacetate, boiling at 52°-60° C./4-7 mmHg.

Workup

  1. waitto stand overnight
  2. customAfter separating off the precipitate
  3. customproduced
  4. distillationthe filtrate was distilled

Sources & evidence

ORD record
ord-3b641bf416d246abb8e05fa8e7f48996
Source dataset
uspto-grants-1984_12
Patent number
US04487781

Reaction notes

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