Hydrochloric Acid → methyl (E) 2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate

HRID 1781563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1781563
[C:1]([O:4][C:5]1[C:13]([CH2:14][CH:15]=[CH2:16])=[C:12]([O:17][CH3:18])[C:11]([CH3:19])=[C:10]2[C:6]=1[C:7](=[O:20])[O:8][CH2:9]2)(=[O:3])[CH3:2].Br[C:22]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C(=O)([O-])[O-].[Ag+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[C:1]([O:4][C:5]1[C:13]([CH2:14]/[CH:15]=[CH:16]/[C:22]2[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])=[C:12]([O:17][CH3:18])[C:11]([CH3:19])=[C:10]2[C:6]=1[C:7](=[O:20])[O:8][CH2:9]2)(=[O:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 10823279Methyl 2-Bromo-3-methylbenzoateHCID 190463174-Acetoxy-5-allyl-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran

Produkt 1

HCID 86749277methyl (E) 2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 178418647HCID 178418647, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-Acetoxy-5-allyl-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran (0.6 g), methyl 2-bromo-3-methylbenzoate (0.92 g), silver carbonate (1.3 g), palladium acetate (0.1 g), triphenylphosphine (0.14 g) and dimethylformamide (70 ml) were heated with stirring at 100° C. for 6 hours, then stirred at ambient temperature for 18 hours. The mixture was poured into ice water and the pH adjusted to 3 by addition of 2N hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was dried and evaporated. The residue was chromatographed on silica gel, eluting with 7:3 hexane:ethyl acetate, to give methyl (E)-2-[3-(4-acetoxy-1,3-dihydro -6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop -1-en-1-yl]-3-methylbenzoate, mp 104°-111° C. (ethyl acetate/hexane).

Aufarbeitung

  1. stirringstirred at ambient temperature for 18 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe extract was dried
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 7:3 hexane

Quellen und Nachweise

ORD-Eintrag
ord-9b1df400bb1d44a4868aff1a360a7ffa
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05633279

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