Toluene → 3-[2-(2-Methoxyethoxy)ethoxy]prop-1-yne

HRID 2297497Notes

Reaction equation

HRID 2297497 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[H-].[Na+].Br[CH2:12][C:13]#[CH:14].C1(C)C=CC=CC=1>C1COCC1.C(OCC)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:14][C:13]#[CH:12]

Participants

7

Reactant 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 8134Diethylene Glycol Monomethyl EtherHCID 24758Sodium hydride

Product 1

HCID 183816833-[2-(2-Methoxyethoxy)ethoxy]prop-1-yneYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution under N2 of 2-(2-methoxy-ethoxy)ethanol (4.9 ml, 41.61 mmoles) in dry THF (50 ml) was portionwise added at room temperature under stirring with 60% NaH in oil (1.66 g, 41.61 mmoles). The mixture was stirred for 30 minutes then dropped into a solution of 80% 3-bromo-propyne in toluene (5.1 ml, 45.77 mmoles), and stirred for 1 hour, then diluted with ethyl ether, thrice washed with water, anhydrified over Na2SO4 and dried to give 5 g of the title compound as an oil (yield: 76%).

Workup

  1. stirringstirred for 1 hour
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-f0716960936b4f84b1e80b342c86670a
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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