Hydrochloric Acid → (E)-methyl 2-(2-[2-(4-fluorophenyl)ethyl]phenyl)-3-methoxypropenoate

HRID 1885801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885801
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:4][CH:3]=1.[CH:21]([O:23][CH3:24])=O.[H-].[Na+].Cl>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2/[C:16](=[CH:21]\[O:23][CH3:24])/[C:17]([O:19][CH3:20])=[O:18])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 19879670Methyl 2-(2-[4-fluorophenyl]ethyl)phenylacetate

Produkt 1

HCID 22845838(E)-methyl 2-(2-[2-(4-fluorophenyl)ethyl]phenyl)-3-methoxypropenoateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of methyl 2-(2-[4-fluorophenyl]ethyl)phenylacetate (2.83g) and methyl formate (12.8ml) in dry DMF (20ml) was added dropwise over 20 minutes to a stirred suspension of sodium hydride (0.50g) in dry DMF (30ml) cooled in an ice bath. Effervescence and foaming built up slowly, and, when it had subsided, the mixture was allowed to warm to room temperature and stir for 3.5 hours. The mixture was diluted with water, acidified with concentrated hydrochloric acid and extracted with ether. The extracts were washed with water, dried and concentrated. A stirred solution of the resulting viscous yellow oil (3.34g) in DMF (30ml) was treated successively with potassium carbonate (3.05g) and dimethyl sulphate (1.54g). After 2 hours, the reaction mixture was poured into water and extracted with ether. The extracts were washed with water, dried, concentrated and chromatographed using 30% ether in petrol to give (E)-methyl 2-(2-[2-(4-fluorophenyl)ethyl]phenyl)-3-methoxypropenoate (2.64g, 81% yield) as a colourless solid m.p. 411/2°-421/2° C., lH NMR (CDCl3); delta 2.76 (4H,br s), 3.70 (3H,s), 3.82 (3H,s), 7.58 (1H,s), ppm.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. extractionextracted with ether
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. additionA stirred solution of the resulting viscous yellow oil (3.34g) in DMF (30ml) was treated successively with potassium carbonate (3.05g) and dimethyl sulphate (1.54g)
  7. waitAfter 2 hours
  8. additionthe reaction mixture was poured into water
  9. extractionextracted with ether
  10. washThe extracts were washed with water
  11. customdried
  12. concentrationconcentrated
  13. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-6fcf5703a69a43cb81d1a7abe8e2c2b4
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05145954

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