Propargyl alcohol → HCID 11469074, compound

HRID 1651364Notes

Reaction equation

HRID 1651364 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[CH3:5][C:6]([CH3:10])=[CH:7][CH2:8]Br>O1CCCC1>[CH3:5][C:6]([CH3:10])=[CH:7][CH2:8][O:4][CH2:1][C:2]#[CH:3]

Participants

4

Reactant 2

HCID 7859Propargyl alcoholHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 11469074HCID 11469074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.5 ml (0.11 mol) of 2-propyn-1-ol in 80 ml of tetrahydrofuran was treated at -78° under argon with 13.5 g (0.12 mol) of potassium tert.-butylate. The mixture was stirred at -78° for 3 hours, 14.1 ml (0.12 mol) of 3,3-dimethylallyl bromide were then added and the mixture was again stirred at -78° for 3 hours and at room temperature for 20 hours. The reaction mixture was poured into ice/water and extracted twice with ether. The combined organic phases were dried over magnesium sulphate and concentrated. There was obtained 1-[(3-methyl-2-butenyl)oxy]-2-propyne as a yellow oil which is processed without purification.

Workup

  1. stirringthe mixture was again stirred at -78° for 3 hours and at room temperature for 20 hours
  2. extractionextracted twice with ether
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b6d7467600d14d42943137bbf7353949
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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