Potassium Carbonate → 4-[3-(1-Adamantyl)-4-(t-butyldimethylsilyloxy)phenyl]-benzaldehyde

HRID 860549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860549
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].[C:12]12([C:22]3[CH:23]=[C:24](Br)[CH:25]=[CH:26][C:27]=3[O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CO.O.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:12]12([C:22]3[CH:23]=[C:24]([C:6]4[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=4)[CH:25]=[CH:26][C:27]=3[O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[CH2:13][CH:14]3[CH2:20][CH:18]([CH2:17][CH:16]([CH2:15]3)[CH2:21]1)[CH2:19]2

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 107883163-(1-Adamantyl)-4-(t-butyldimethylsilyloxy)bromobenzene

Produkt 1

HCID 113853054-[3-(1-Adamantyl)-4-(t-butyldimethylsilyloxy)phenyl]-benzaldehydeAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21867641Toluene methanolLösungsmittel

Versuchsvorschrift

A mixture of 4-formylphenyl boronic acid (0.301 g, 2.00 mmol), 3-(1-adamantyl)-4-(t-butyldimethylsilyloxy)bromobenzene (0.768 g, 1.82 mmol, prepared in a similar manner as described by Charpentier, B. et al. in J. Med. Chem. 1995, 38, 4993–5006) and potassium carbonate (0.757 g, 5.47 mmol) in 60 mL of toluene:methanol (4:1) and water (2 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine) palladium(0) (0.422 g, 0.36 mmol) was added and the mixture heated at reflux for 19 hours. 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 (eluent: hexane:EtOAc, 97:3) to give 0.500 g of 4-[3-(1-adamantyl)-4-(t-butyldimethylsilyloxy)phenyl]-benzaldehyde (78%) as a solid. 1H NMR (300 MHz; CDCl3): 0.38 (s, 6H), 1.07 (s, 9H), 1.79 (s, 6H), 2.10–2.17 (m, 9H), 6.89 (d, J=8.7 Hz, 1H), 7.34 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.52 (d, J=2.4 Hz, 1H), 7.71 (d, J=8.1 Hz, 2H), 7.91 (d, J=8.1 Hz, 2H), 10.02 (brs, 1H).

Aufarbeitung

  1. customprepared in a similar manner
  2. temperaturethe mixture heated
  3. temperatureat reflux for 19 hours
  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 (eluent: hexane:EtOAc, 97:3)

Quellen und Nachweise

ORD-Eintrag
ord-1c8da66cc81748a0a8a579bab108a655
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153875B2

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