4-Diethylamino-3-isopropylbenzaldehyde → 1-(4-Diethylamino-3-isopropylphenyl)prop-2-yn-1-ol

HRID 1698422Notes

Reaction equation

HRID 1698422 reaction equation
[C:1]([Mg]Br)#[CH:2].C1COCC1.[CH2:10]([N:12]([CH2:24][CH3:25])[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[CH:21]([CH3:23])[CH3:22])[CH3:11]>>[CH2:24]([N:12]([CH2:10][CH3:11])[C:13]1[CH:20]=[CH:19][C:16]([CH:17]([OH:18])[C:1]#[CH:2])=[CH:15][C:14]=1[CH:21]([CH3:23])[CH3:22])[CH3:25]

Participants

3

Reactant 2

HCID 866465754-Diethylamino-3-isopropylbenzaldehydeHCID 178462450HCID 178462450, compound

Product 1

HCID 866465761-(4-Diethylamino-3-isopropylphenyl)prop-2-yn-1-olYield 83.8%

Procedure

In a manner analogous to example 1 e, the process is carried out by a reaction of 9.3 ml (4.7 mmol) of 0.5M ethynylmagnesium bromide/THF with 780 mg (3.5 mmol) of 4-diethylamino-3-isopropylbenzaldehyde. 720 mg of 1-(4-diethylamino-3-isopropylphenyl)prop-2-yn-1-ol are obtained in the form of a yellow oil (yield=83%).

Sources & evidence

ORD record
ord-852eb9d6920844f5aa413700470ec0e6
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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