2-Methyl-3-butyn-2-ol → 6-Hepten-3-yn-2-ol, 2,6-dimethyl-

HRID 484566Notes

Reaction equation

HRID 484566 reaction equation
[CH3:1][C:2]([OH:6])([C:4]#[CH:5])[CH3:3].Cl[CH2:8][C:9]([CH3:11])=[CH2:10].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:1][C:2]([OH:6])([C:4]#[C:5][CH2:10][C:9]([CH3:11])=[CH2:8])[CH3:3]

Participants

5

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate

Product 1

HCID 143221006-Hepten-3-yn-2-ol, 2,6-dimethyl-Yield 65%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

The coupling reaction was conducted in the manner described in the procedure of Example VI using the following reagents: 1.00 mL (10.3 mmoles) of 2-methyl-3-butyn-2-ol, 1.10 mL (11.1 mmoles) of 3-chloro-2-methylpropene, 2.34 g (16.9 mmoles) of anhydrous potassium carbonate, 89 mg (0.90 mmole) of cuprous chloride, and 165 mg (0.72 mmole) of benzyltriethylammonium chloride. Isolation of the product in the usual manner afforded 925 mg (65%) of the named alcohol, thereby demonstrating the lack of need for a solvent in this coupling reaction.

Workup

  1. customThe coupling reaction

Sources & evidence

ORD record
ord-d17dfcd1bd7f4f7f934de630027e17ea
Source dataset
uspto-grants-1993_07
Patent number
US05231232

Reaction notes

Loading…