2,6-Dimethylaniline → HCID 12010733, Verbindung

HRID 429598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 429598
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH3:13])[O:12][CH2:11][CH2:10][O:9]1.[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH2:17].CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH:17][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH3:13])[O:12][CH2:11][CH2:10][O:9]1

Komponenten

7

Edukt 3

HCID 68962,6-DimethylanilineHCID 6152842-(2-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 12010733HCID 12010733, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 2-(2′-bromophenyl)-2-methyl-1,3-dioxolane (362 mg, 1.49 mmol), 2,6-dimethylaniline(189 mg, 1.56 mmol), NaOtBu (172 mg, 1.79 mmol), Pd(dba)2 (17 mg, 0.03 mmol), ligand A (21 mg, 0.06 mmol) in toluene (4 mL) was heated to 105° C. for 4.5 hours. The reaction was cooled to room temperature, taken up in diethyl ether (125 mL), washed with water (2×30 mL) and brine (30 mL), dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel using hexane (or hexanes: ethyl acetate) as the eluent to afford compound 2b-1, after drying under vacuum, as an off-white solid (yield: 391 mg, 93%) 1H NMR (CDCl3): δ7.41 (dd, 1H, J=7.8, 1.8 Hz, ArH), 7.13-6.99 (m, 4H, ArH), 6.70 (dt, 1H, J=7.5, 1.2 Hz, ArH), 6.15 (dd, 1H, J=7.8, 0.9, ArH), 4.12 (m, 2H, O—CH—CH—O), 3.93 (m, 2H, O—CH—CH—O), 2.18 (s, 6H, Ar—CH3), 1.84 (s, 3H, CH3). 13C NMR (CDCl3): δ143.5, 138.6, 135.2, 129.1, 128.5, 126.3, 125.6, 125.2, 117.3, 112.6, 109.8, 64.1, 24.1, 18.3. Anal. for C18H21NO2; Calcd: C, 76.29, H, 7.47; N, 4.94; Found: C, 75.86; H, 7.46; N, 4.89.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water (2×30 mL) and brine (30 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by column chromatography on silica gel
  7. customto afford compound 2b-1
  8. dry with materialafter drying under vacuum, as an off-white solid (yield: 391 mg, 93%) 1H NMR (CDCl3): δ7.41 (dd, 1H, J=7.8, 1.8 Hz, ArH), 7.13-6.99 (m, 4H, ArH), 6.70 (dt, 1H, J=7.5, 1.2 Hz, ArH), 6.15 (dd, 1H, J=7.8, 0.9, ArH), 4.12 (m, 2H, O—CH—CH—O), 3.93 (m, 2H, O—CH—CH—O), 2.18 (s, 6H, Ar—CH3), 1.84 (s, 3H, CH3)

Quellen und Nachweise

ORD-Eintrag
ord-1f24f6e5335f45748a36c3ff94e91552
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316663B1

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