Isopropanol → 2-(2-Chloro-4-isopropoxyphenoxy)-1,3-thiazole

HRID 404894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404894
[Cl:1][C:2]1[CH:3]=[C:4]([OH:14])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1.[CH:15](O)([CH3:17])[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH:15]([CH3:17])[CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 691693943-Chloro-4-(1,3-thiazol-2-yloxy)phenol

Produkt 1

HCID 694369042-(2-Chloro-4-isopropoxyphenoxy)-1,3-thiazoleAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of Example 9B (2.3 g, 0.01 mol), isopropanol (1.2 mL, 0.015 mol) and triphenylphosphine (3.93 g, 0.015 mol) in dry tetrahydrofuran was added diethyl azodicarboxylate (2.61 g, 0.015 mol) drop wise and the reaction was stirred at room temperature overnight. The solvent was removed and the residue was purified on silica gel (ethyl acetate/hexane, 5˜35%) to give 2.4 g of product as a light yellow oil (89% yield), 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (d, J=5.88 Hz, 6H) 4.42-4.57 (m, 1H) 6.76-6.86 (m, 2H) 6.99 (d, J=2.94 Hz, 1H) 7.19 (d, J=3.68 Hz, 1H) 7.23 (s, 1H), MS (ESI) m/z 269.9 (M+H)+.

Aufarbeitung

  1. customThe solvent was removed
  2. customthe residue was purified on silica gel (ethyl acetate/hexane, 5˜35%)

Quellen und Nachweise

ORD-Eintrag
ord-97f736f9d04f494ca8469431e78d3212
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748627B2

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