Potassium Carbonate → 3-(3,3-Dimethyl-5-propionyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde

HRID 460293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460293
[CH3:1][C:2]1([CH3:24])[C:6]2[CH:7]=[C:8]([C:20](=[O:23])[CH2:21][CH3:22])[CH:9]=[C:10](B3OC(C)(C)C(C)(C)O3)[C:5]=2[O:4][CH2:3]1.Br[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][C:35]([F:38])([F:37])[F:36])[CH:29]=[O:30].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:24][C:2]1([CH3:1])[C:6]2[CH:7]=[C:8]([C:20](=[O:23])[CH2:21][CH3:22])[CH:9]=[C:10]([C:32]3[CH:31]=[C:28]([CH:27]=[CH:26][C:33]=3[O:34][C:35]([F:36])([F:37])[F:38])[CH:29]=[O:30])[C:5]=2[O:4][CH2:3]1

Komponenten

9

Edukt 3

HCID 11430Potassium CarbonateHCID 131504163-Bromo-4-(trifluoromethoxy)benzaldehydeHCID 184453891-[3,3-Dimethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-5-yl]-propan-1-one

Produkt 1

HCID 184453993-(3,3-Dimethyl-5-propionyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehydeAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1-[3,3-dimethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-5-yl]-propan-1-one (1.33 g, 4.05 mmol), 3-bromo-4-trifluoromethoxybenzaldehyde (example 1h) (1.09 g, 4.05 mmol) and potassium carbonate (1.12 g, 8.10 mmol) in toluene (12 mL), ethanol (2.4 mL) and water (1.5 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (234 mg, 0.20 mmol) was added and the mixture heated at reflux under argon for 19 hrs. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (10% ethyl acetate in hexane) to give 1.17 g of 3-(3,3-dimethyl-5-propionyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde (50%). 1H NMR (300 MHz; CDCl3): 1.23 (t, J=7.2 Hz, 3H), 1.42 (s, 6H), 2.99 (q, J=7.2 Hz, 2H), 4.34 (s, 2H), 7.52 (dd, J1=7.2 Hz, J2=1.8 Hz, 1H), 7.84 (d, J=2.1 Hz, 1H), 7.85 (d, J=2.13 Hz, 1H), 7.96 (dd, J1=8.4 Hz, J2=2.1 Hz, 1H), 8.03 (d, J=2.1 Hz, 1H), 10.05 (s, 1H).

Aufarbeitung

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon for 19 hrs
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f19ed56a81fd4efdadef39c40b868554
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196108B2

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