Sodium Carbonate → 6-[3-(t-Butyl)-4-methoxyphenyl]-2-naphthaldehyde

HRID 860557Notizen

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Reaktionsgleichung von HRID 860557
[C:1]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].Br[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([CH:27]=[O:28])[CH:21]=[CH:20]2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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:1]([C:5]1[CH:6]=[C:7]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([CH:27]=[O:28])[CH:21]=[CH:20]3)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 106321513-Tert-butyl-4-methoxyphenylboronic acidHCID 134770296-Bromonaphthalene-2-carbaldehyde

Produkt 1

HCID 865860436-[3-(t-Butyl)-4-methoxyphenyl]-2-naphthaldehydeAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(t-butyl)-4-methoxyphenyl boronic acid (0.424 g, 2.04 mmol), 6-bromo-2-naphthaldehyde (0.400 g, 1.70 mmol) and sodium carbonate (0.541 g, 5.10 mmol) in 10 mL of toluene:ethanol (4:1) and water (1 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine) palladium(0) (0.059 g, 0.05 mmol) was added and the mixture heated at reflux for 17 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, 9:1) to give 0.50 g of 6-[3-(t-butyl)-4-methoxyphenyl]-2-naphthaldehyde (76%) as a solid. 1H NMR (300 MHz; DMSO-d6, 300 MHz): 1.46 (s, 9H), 3.92 (s, 3H), 7.02 (d, J=8.7 Hz, 1H), 7.57 (dd, J1=8.7 Hz, J2=2.4 Hz, 1H), 7.66 (d, J=2.4 Hz, 1H), 7.84 (dd, J1=8.4 Hz, J2=1.8 Hz, 1H), 7.97 (brs, 2H), 8.04 (s, 1H), 8.05 (d, J=8.7 Hz, 1H), 8.35 (s, 1H), 10.16 (s, 1H).

Aufarbeitung

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux for 17 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, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-112492b17dad4e7aa63468d8b3f3dcfc
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153875B2

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