Magnesium → 1-Cyclopropyl-1-(4-chlorophenyl)-4-cyano-4-(3-phenoxyphenyl)butane

HRID 1588879Notes

Reaction equation

HRID 1588879 reaction equation
[CH:1]1([CH:4]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:5][CH:6]=[C:7]([C:21]#[N:22])[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)[CH2:3][CH2:2]1.[Mg]>CO.Cl>[CH:1]1([CH:4]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:5][CH2:6][CH:7]([C:21]#[N:22])[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 5462224MagnesiumHCID 544107201-Cyclopropyl-1-(4-chlorophenyl)-4-cyano-4-(3-phenoxyphenyl)-3-butene

Product 1

HCID 197548591-Cyclopropyl-1-(4-chlorophenyl)-4-cyano-4-(3-phenoxyphenyl)butaneYield 87.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.9 gram (0.002 mole) of 1-cyclopropyl-1-(4-chlorophenyl) -4-cyano-4-(3-phenoxyphenyl)-3-butene in 15 ml of methanol was stirred, and 0.5 gram (0.002 mole) of magnesium was added. The reaction mixture was stirred for about one hour at which time an exothermic reaction occurred. The reaction mixture was cooled to 0° C. where it was stirred for one hour, and then it was allowed to warm to ambient temperature where it stirred for two hours. After this time the reaction mixture was diluted with 20 ml of aqueous 10% hydrochloric acid, and the mixture was extracted with diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 0.7 gram of 1-cyclopropyl-1-(4-chlorophenyl)-4-cyano-4-(3-phenoxyphenyl)butane. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customan exothermic reaction
  2. stirringwas stirred for one hour
  3. temperatureto warm to ambient temperature where it
  4. stirringstirred for two hours
  5. extractionthe mixture was extracted with diethyl ether
  6. dry with materialThe combined extracts were dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e8ef1404c248414b9abcee41d4f2b800
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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