Propargyl alcohol → HCID 13044974, compound

HRID 615560Notes

Reaction equation

HRID 615560 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:13]([OH:16])[C:14]#[CH:15]>Cl[Cu]>[CH2:13]([OH:16])[C:14]#[C:15][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 7859Propargyl alcoholHCID 12400864(Z)-1-chloro-2-undecene

Product 1

HCID 13044974HCID 13044974, compound

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

By the procedure of example 13, (Z)-1-chloro-2-undecene (4.0 g, 21 mmol), the Grignard complex of propargyl alcohol (prepared from 35 mmol of propargyl alcohol and 70 mmol of ethylmagnesium bromide in 35 ml of dry THF), and 252 mg of CuCl were allowed to react at 50° C. for 20 h. under argon. Workup of the reaction mixture and purification of the crude product as described before in example 13 gave 2.54 g (58% by weight yield) of (Z)-5-tetradecen-2-yn-1-ol as a colorless oil, bp 102°-127° C./0.25 mmHg (evaporative distillation).

Workup

  1. customto react at 50° C. for 20 h. under argon
  2. customWorkup of the reaction mixture and purification of the crude product
  3. customgave
  4. distillation2.54 g (58% by weight yield) of (Z)-5-tetradecen-2-yn-1-ol as a colorless oil, bp 102°-127° C./0.25 mmHg (evaporative distillation)

Sources & evidence

ORD record
ord-949139f4e0b34924bca410458ab24f82
Source dataset
uspto-grants-1985_02
Patent number
US04500462

Reaction notes

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