2-Methoxybenzaldehyde → 1-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

HRID 845161Notes

Reaction equation

HRID 845161 reaction equation
C(C1C=C(C(C)C)C=C(C(C)C)C=1S(NN=[C:21]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])(=O)=O)(C)C.[CH:33](=[O:42])[C:34]1[C:35](OC)=[CH:36][CH:37]=[CH:38][CH:39]=1>>[CH:34]1([CH:33]([OH:42])[C:21]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:22][CH2:23][N:24]([CH3:25])[CH3:26])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1

Participants

3

Reactant 2

HCID 86582-MethoxybenzaldehydeHCID 86741729beta-Dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone

Product 1

HCID 538458471-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-olYield 60.3%

Procedure

By using a method similar to that described in Example 22, but starting from β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (20 g) and from o-anisaldehyde (6.5 g), 4-dimethylamino-1-(2-methoxyphenyl)-2-phenyl-2-buten-1-ol (Z) (7.2 g) is obtained in the form of a white powder melting at 77° C. after recrystallisation from a mixture (85 cc) of petroleum ether and isopropyl ether (70/30 by volume).

Sources & evidence

ORD record
ord-d743bb2c0a394fb3a261485e0e704ddb
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

Loading…