3-Butyn-1-OL → HCID 19373391, compound

HRID 129301Notes

Reaction equation

HRID 129301 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][C:5]#[CH:6].Br[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>C1(C)C=CC=CC=1>[CH2:3]([O:7][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][C:5]#[CH:6]

Participants

5

Reactant 3

HCID 135663-Butyn-1-OLHCID 24758Sodium hydrideHCID 68320Ethyl 3-bromopropionate

Product 1

HCID 19373391HCID 19373391, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium hydride (4.6 g of 60% dispersion in mineral oil) was added to a stirred solution of but-3-yn-1-ol (16.2 g, 0.23 mol, Lancaster) in dry toluene (200 ml). After stirring for 2 hours at 25° C. a solution of ethyl 3-bromopropionate (20.8 g, 0.115 mol, Lancaster) was added. The reaction mixture was stirred and refluxed for 7 hours. Ethyl 3-(but-3-ynyloxy)propionate (17.8 g) was obtained by quenching the cooled reaction mixture in water, extracting with ether, washing with brine, drying over anhydrous magnesium sulphate followed by evaporation.

Workup

  1. additionwas added
  2. temperaturerefluxed for 7 hours

Sources & evidence

ORD record
ord-032ef0aa54bf4c889264aa035b465d5b
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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