Pyridine → Acetic Acid 3-(4-phenoxy-quinazolin-6-yl)-allyl ester

HRID 1264056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264056
[O:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[CH:19][CH2:20][OH:21])[CH:16]=2)[N:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl.Cl>[O:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[CH:19][CH2:20][O:21][C:28](=[O:30])[CH3:29])[CH:16]=2)[N:11]=[CH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 694856033-(4-Phenoxy-quinazolin-6-yl)-prop-2-en-1-ol

Produkt 1

HCID 69484701Acetic Acid 3-(4-phenoxy-quinazolin-6-yl)-allyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To alcohol 25 (900 mg, 3.23 mmol) and pyridine (0.8 mL, 10 mmol) in dry CH2Cl2 (15 mL) at 0° C. was added acetyl chloride (0.3 mL, 4.2 mmol). The resulting mixture was stirred for 2 hours, the diluted with CH2Cl2 (10 mL) and 5% HCl (10 mL). The mixture was transferred to a separatory funnel and the organic layer washed with H2O and brine. The organic layer was dried (Na2SO4), solids filtered and the solvent removed in vacuo to provide the desired acetate 26 as a yellow waxy solid (1.04 g, 100%).1H NMR (CDCl3; 400 MHz): δ: 8.72 (s, 1H), 8.30 (d, 1H, J=1.7 Hz), 7.98 (m, 2H), 7.49 (m, 2H), 7.30 (m, 1H), 7.25 (m, 2H), 6.84 (d, 1H, J=16.0 Hz), 6.46 (m, 1H), 4.79 (dd, 2H, J=6.2 Hz, 1.2 Hz), 2.11 (s, 3H).

Aufarbeitung

  1. customThe mixture was transferred to a separatory funnel
  2. washthe organic layer washed with H2O and brine
  3. dry with materialThe organic layer was dried (Na2SO4), solids
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-957b8fa3c8f5490c9c8b98e5b1ae2eb2
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541481B2

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