3-Tert-butyl-4-dimethylaminobenzaldehyde → 1-(3-Tert-butyl-4-dimethylaminophenyl)prop-2-yn-1-ol

HRID 1698401Notes

Reaction equation

HRID 1698401 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[N:13]([CH3:15])[CH3:14])[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[C:16]([Mg]Br)#[CH:17]>>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]([OH:9])[C:16]#[CH:17])[CH:10]=[CH:11][C:12]=1[N:13]([CH3:15])[CH3:14])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 866465663-Tert-butyl-4-dimethylaminobenzaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 866465671-(3-Tert-butyl-4-dimethylaminophenyl)prop-2-yn-1-ol

Procedure

In a manner analogous to example 1 e, the process is carried out by a reaction of 1 g (4.9 mmol) of 3-tert-butyl-4-dimethylaminobenzaldehyde with 12 ml (6 mmol) of a 0.5M solution of ethynylmagnesium bromide. 900 mg of 1-(3-tert-butyl-4-dimethylaminophenyl)prop-2-yn-1-ol are obtained in the form of a colourless oil (yield=79%).

Sources & evidence

ORD record
ord-c17b1a62f980476c873f93b20d324d4b
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

Loading…