Magnesium → HCID 54287504, compound

HRID 1588889Notes

Reaction equation

HRID 1588889 reaction equation
[CH:1]1([C:4]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)[CH3:8])[CH2:3][CH2:2]1.[Mg]>CO.C(O)C>[CH:1]1([CH:4]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:5]=[CH:6][CH:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:10]=2)[CH3:8])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 5462224MagnesiumHCID 86747009HCID 86747009, compound

Product 1

HCID 54287504HCID 54287504, compoundYield 5.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 0.40 gram (0.01 mole) of 1-cyclopropyl-1-(4-chlorophenyl)-4-(4-fluoro-3-phenoxyphenyl)-1,3-pentadiene and 2.43 grams (0.1 mole) of magnesium in 25 ml of methanol and 5 ml of ethanol was vigorously stirred for about 18 hours at ambient temperature. After this time the reaction was quenched with aqueous 3N hydrochloric acid, and the reaction mixture was extracted with two 25 ml portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 0.23 gram of 1-cyclopropyl-1-(4-chlorophenyl)-4-(4-fluoro-3-phenoxyphenyl)-2-pentene. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customAfter this time the reaction was quenched with aqueous 3N hydrochloric acid
  2. extractionthe reaction mixture was extracted with two 25 ml portions of diethyl ether
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7a11074c382b4485b432192af1de1752
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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