o-Fluorobenzaldehyde → 1-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

HRID 845158Notes

Reaction equation

HRID 845158 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.F[C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH:36]=[O:37]>>[CH:35]1([CH:36]([OH:37])[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])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:34]1

Participants

3

Reactant 2

HCID 67970o-FluorobenzaldehydeHCID 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 (10 g) and 2-fluorobenzaldehyde (2.6 cc), 4-dimethylamino-1-(2-fluorophenyl)-2-phenyl-2-buten-1-ol (Z) hydrochloride (3.5 g) is obtained in the form of a white powder melting at 175° C. after recrystallisation from a mixture (90 cc) of isopropanol and isopropyl ether (60/40 by volume).

Sources & evidence

ORD record
ord-d28cc7bc5a4d4d2f88beb9dfa75ee670
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

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