Magnesium → Methyl 3-cyclopropyl-3-(4-chlorophenyl)propanoate

HRID 1588875Notes

Reaction equation

HRID 1588875 reaction equation
[CH:1]1([C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:5][C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.[Mg]>CO.Cl>[CH:1]1([CH:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 5462224MagnesiumHCID 53818028Methyl 3-cyclopropyl-3-(4-chlorophenyl)propenoate

Product 1

HCID 19754833Methyl 3-cyclopropyl-3-(4-chlorophenyl)propanoateYield 62.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 17.0 grams (0.072 mole) of methyl 3-cyclopropyl-3-(4-chlorophenyl)propenoate and 4.3 grams (0.18 mole) of magnesium in 250 ml of methanol was stirred at ambient temperature for about 3.5 hours. After this time the reaction mixture was carefully diluted with aqueous 3N hydrochloric acid. The mixture was extracted with diethyl ether. The combined ether extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was distilled under vacuum, yielding 10.7 grams of methyl 3-cyclopropyl-3-(4-chlorophenyl)propanoate; b.p. 91-97° C./0.10 mm. The spectrum was consistent with the proposed structure.

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. dry with materialThe combined ether extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  5. distillationThe oil was distilled under vacuum

Sources & evidence

ORD record
ord-347316cf47e34dd3b75935a93eb9ab0b
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

Loading…