4-Dimethylamino-3,5-diisopropylbenzaldehyde → 1-(4-Dimethylamino-3,5-diisopropylphenyl)prop-2-yn-1-ol

HRID 1698418Notes

Reaction equation

HRID 1698418 reaction equation
[C:1]([Mg]Br)#[CH:2].C1COCC1.[CH3:10][N:11]([CH3:26])[C:12]1[C:19]([CH:20]([CH3:22])[CH3:21])=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][C:13]=1[CH:23]([CH3:25])[CH3:24]>>[CH3:10][N:11]([CH3:26])[C:12]1[C:19]([CH:20]([CH3:21])[CH3:22])=[CH:18][C:15]([CH:16]([OH:17])[C:1]#[CH:2])=[CH:14][C:13]=1[CH:23]([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 866465744-Dimethylamino-3,5-diisopropylbenzaldehydeHCID 178462450HCID 178462450, compound

Product 1

HCID 866465731-(4-Dimethylamino-3,5-diisopropylphenyl)prop-2-yn-1-olYield 192.8%

Procedure

In a manner analogous to example 1 e, the process is carried out by a reaction of 28 ml (14 mmol) of 0.5M ethynylmagnesium bromide/THF with 1.2 g (5 mmol) of 4-dimethylamino-3,5-diisopropylbenzaldehyde. 2.5 g of 1-(4-dimethylamino-3,5-diisopropylphenyl)prop-2-yn-1-ol are obtained in the form of a whitish solid (yield=90%).

Sources & evidence

ORD record
ord-5aee3e70ec1c4aae994561a41b13c48e
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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