Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate → Ethyl 5-(3-methoxypropyl)-2-phenylthiazole-4-carboxylate

HRID 1799109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799109
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CCOC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

3

Edukt 1

HCID 67425118Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate

Produkt 1

HCID 67425119Ethyl 5-(3-methoxypropyl)-2-phenylthiazole-4-carboxylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate (26.1 g, 86.6 mmol) was dissolved in EtOAc (350 mL) and hydrogenated under balloon pressure for four days until LCMS indicated complete reduction of unsaturation. On day three, the catalyst was removed by filtration, fresh catalyst added and the mixtures re-subjected to hydrogenation at balloon pressure. The catalyst was removed by filtration through a pad of celite. The filter pad was rinsed with EtOAc and the filtrate concentrated to dryness. The crude product was purified by MPLC eluting with pentane/EtOAc to give ethyl 5-(3-methoxypropyl)-2-phenylthiazole-4-carboxylate (23.2 g, 88% yield).

Aufarbeitung

  1. waitOn day three
  2. customthe catalyst was removed by filtration, fresh catalyst
  3. additionadded
  4. customThe catalyst was removed by filtration through a pad of celite
  5. washThe filter pad was rinsed with EtOAc
  6. concentrationthe filtrate concentrated to dryness
  7. customThe crude product was purified by MPLC
  8. washeluting with pentane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-f1c187a9cd5a4096b4646c7aaf1c658f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343997B2

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