3-Bromobenzaldehyde → 1-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

HRID 845159Notes

Reaction equation

HRID 845159 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.Br[C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH:37]=[O:38]>>[CH:36]1([CH:37]([OH:38])[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])[CH2:39][CH2:40][CH2:41][CH2:34][CH2:35]1

Participants

3

Reactant 2

HCID 765833-BromobenzaldehydeHCID 86741729beta-Dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone

Product 1

HCID 538458471-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

Procedure

By using a method similar to that described in Example 22, but starting from β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (20 g) and 3-bromobenzaldehyde (5.6 cc), 1-(3-bromophenyl)-4-dimethylamino-2-phenyl-2-buten-1-ol (Z) hydrochloride (11.3 g) is obtained in the form of a white solid melting at 188° C. after recrystallisation from isopropanol (200 cc).

Sources & evidence

ORD record
ord-99a03d4a9a6b4b5783d5a06c43667b5d
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

Loading…