4-Methylpyridine → HCID 20223436, Verbindung

HRID 1249584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1249584
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.C1([Li])C=CC=CC=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:30]=[CH:31][CH:32]=1)[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)=[O:21]>O1CCCC1>[CH3:29][O:28][C:24]1[CH:23]=[C:22]([C:20]([C:19]2[CH:30]=[CH:31][CH:32]=[C:17]([O:16][CH3:15])[CH:18]=2)([OH:21])[CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:27]=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 79634-MethylpyridineHCID 12548810Bis(3-methoxyphenyl)methanoneHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 20223436HCID 20223436, VerbindungAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-picoline (32,5 g) in tetrahydrofuran (140 ml), was added dropwise under argon a solution of phenyl lithium in 7:3 cyclohexane-ether (1.9M; 184 ml) at such a rate that the reaction temperature could be maintained at 10°-20° by means of an external cooling bath. After the addition was completed, the reaction was cooled to -5°, and then a solution of 3,3'-dimethoxybenzophenone (77.4 g) in dry tetrahydrofuran (140 ml) was added so that the reaction temperature did not exceed 0°. The cooling bath was removed and the mixture was stirred at room temperature for two hours, whereupon water (140 ml) was added slowly followed by tetrahydrofuran (140 ml). The layers were separated, and after sodium chloride (~30 g) was added to the aqueous phase, it was reextracted with tetrahydrofuran (2×100 ml). The combined organic layers were washed with brine (50 ml), then were dried (over sodium sulfate) and evaporated. The crude product was triturated with hot hexane (2×300 ml) and the resulting solid was filtered to give 93.5 g of alpha,alpha-bis(3-methoxyphenyl)-4-pyridineethanol, mp 134°-135°.

Aufarbeitung

  1. temperaturecould be maintained at 10°-20° by means of an external cooling bath
  2. additionAfter the addition
  3. temperaturethe reaction was cooled to -5°
  4. customdid not exceed 0°
  5. customThe cooling bath was removed
  6. additionwas added slowly
  7. customThe layers were separated
  8. additionafter sodium chloride (~30 g) was added to the aqueous phase, it
  9. washThe combined organic layers were washed with brine (50 ml)
  10. dry with materialwere dried (over sodium sulfate)
  11. customevaporated
  12. customThe crude product was triturated with hot hexane (2×300 ml)
  13. filtrationthe resulting solid was filtered

Quellen und Nachweise

ORD-Eintrag
ord-31701775007047d49175a645070562fd
Quelldatensatz
uspto-grants-1986_12
Patentnummer
US04632925

Notizen zur Reaktion

Wird geladen…