Acetone → 1-(1-Hydroxy-1,2,3,4-tetrahydro-1-naphthyl)-3-dimethylamino-1-phenyl-1-propene

HRID 845170Notes

Reaction equation

HRID 845170 reaction equation
[CH3:1][N:2]([CH3:13])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.P(Cl)(Cl)(Cl)=O.Cl[C:20]1[CH:21]=[C:22](S)[CH:23]=[CH:24][CH:25]=1.[C:27]([BH3-])#N.[Na+].Cl.[CH3:32][C:33]([CH3:35])=[O:34]>C(OCC)C>[OH:34][C:33]1([C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH2:3][N:2]([CH3:13])[CH3:1])[C:35]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:25][CH2:27][CH2:32]1

Participants

8

Reactant 6

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 162573-ChlorothiophenolHCID 24813Phosphorus oxychlorideHCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 544490061-(1-Hydroxy-1,2,3,4-tetrahydro-1-naphthyl)-3-dimethylamino-1-phenyl-1-propene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (5 g), phosphorus oxychloride (2.5 cc), 3-chlorothiophenol (4.13 g) and sodium cyanoborohydride (1 g), and after evaporating the organic phase to dryness under reduced pressure (2.7 kPa) at 40° C., a residue is obtained which is dissolved in a mixture (20 cc) of acetone and ethyl ether (50/50 by volume). A 5.6N solution (6 cc) of hydrochloric acid gas in ethyl ether is added to this solution. The precipitate formed is separated off by filtration and then recrystallised from isopropanol (30 cc). In this way 3-(3-chlorophenylthio)-1-dimethylamino-3-phenyl-2-propene (Z) hydrochloride (2.6 g) is obtained in the form of a white solid melting at 156°-157° C.

Workup

  1. customafter evaporating the organic phase to dryness under reduced pressure (2.7 kPa) at 40° C.
  2. customa residue is obtained which
  3. customThe precipitate formed
  4. customis separated off by filtration
  5. customrecrystallised from isopropanol (30 cc)

Sources & evidence

ORD record
ord-94c95fc40b4341e69b88dbd4138fec0f
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

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