3-(1,1-Dimethylethyl)-4-(1-pyrrolidinyl)benzaldehyde → HCID 86646568, compound

HRID 1698405Notes

Reaction equation

HRID 1698405 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[C:18]([Mg]Br)#[CH:19]>>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]([OH:9])[C:18]#[CH:19])[CH:10]=[CH:11][C:12]=1[N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 860427013-(1,1-Dimethylethyl)-4-(1-pyrrolidinyl)benzaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 86646568HCID 86646568, compound

Procedure

In a manner analogous to example 1 e, the process is carried out by a reaction of 1 g (4 mmol) of 3-tert-butyl-4-pyrrolidin-1-ylbenzaldehyde with 11 ml (5.5 mmol) of a 0.5M solution of ethynylmagnesium bromide. 640 mg of 1-(3-tert-butyl-4-pyrrolidin-1-ylphenyl)prop-2-yn-1-ol are obtained in the form of a colourless oil (yield=62%).

Sources & evidence

ORD record
ord-974beb146d6c4cc5bf79c3a4b2be207a
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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