Hydrochloric Acid → (1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione

HRID 407857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407857
Br[C:2]1[CH:3]2[O:11][CH:9]([CH:10]=1)[CH:8]1[CH:4]2[C:5](=[O:22])[CH:6]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[C:7]1=[O:12].[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:3]3[O:11][CH:9]([CH:10]=2)[CH:8]2[CH:4]3[C:5](=[O:22])[CH:6]([C:13]3[C:14]([CH3:21])=[CH:15][C:16]([CH3:20])=[CH:17][C:18]=3[CH3:19])[C:7]2=[O:12])=[CH:26][CH:25]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 23693092Sodium 2'-(dicyclohexylphosphanyl)-2,6-dimethoxy(1,1'-biphenyl)-3-sulfonate--water (1/1/1)HCID 67284125(1RS, 2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

Produkt 1

HCID 67283881(1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of (1RS,2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione (300 mg, 0.82 mmol), 4-fluorophenylboronic acid (171 mg, 1.22 mmol), sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1-biphenyl-3-sulfonate hydrate (17 mg, 0.03 mmol), potassium phosphate (522 mg, 2.5 mmol) and palladium acetate (4 mg, 0.02 mmol) in water (8 ml) are heated for 150° C. for 25 minutes under microwave irradiation. The mixture is cooled to room temperature and dilute aqueous hydrochloric acid is added. The mixture is filtered and the filtrate is extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. Purification by column chromatography on silica gel gives (1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione.

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationThe mixture is filtered
  3. extractionthe filtrate is extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customPurification by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3cbf642752874ed7bf5be552f8d94916
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754242B2

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