3-Tert-butyl-5-chloro-4-dimethylaminobenzaldehyde → 1-(3-Tert-butyl-5-chloro-4-dimethylaminophenyl)prop-2-yn-1-ol

HRID 1698414Notes

Reaction equation

HRID 1698414 reaction equation
[C:1]([Mg]Br)#[CH:2].C1COCC1.[C:10]([C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([Cl:25])[C:21]=1[N:22]([CH3:24])[CH3:23])[CH:17]=[O:18])([CH3:13])([CH3:12])[CH3:11]>>[C:10]([C:14]1[CH:15]=[C:16]([CH:17]([OH:18])[C:1]#[CH:2])[CH:19]=[C:20]([Cl:25])[C:21]=1[N:22]([CH3:23])[CH3:24])([CH3:13])([CH3:11])[CH3:12]

Participants

3

Reactant 2

HCID 866465713-Tert-butyl-5-chloro-4-dimethylaminobenzaldehydeHCID 178462450HCID 178462450, compound

Product 1

HCID 866465721-(3-Tert-butyl-5-chloro-4-dimethylaminophenyl)prop-2-yn-1-olYield 48.9%

Procedure

In a manner analogous to example 1 e, the process is carried out by a reaction of 13 ml (6.5 mmol) of 0.5M ethynylmagnesium bromide/THF with 1.2 g (5 mmol) of 3-tert-butyl-5-chloro-4-dimethylaminobenzaldehyde. 650 mg of 1-(3-tert-butyl-5-chloro-4-dimethylamino-phenyl)prop-2-yn-1-ol are obtained in the form of a yellow solid (yield=49%).

Sources & evidence

ORD record
ord-286eba363b8c4dfc9c38ef76ec6b142b
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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