Diisobutylaluminum hydride → 3-(4-Phenoxy-quinazolin-6-yl)-prop-2-en-1-ol

HRID 1264055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264055
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][N:10]=[C:9]2[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[O:16]([C:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH:5]=[CH:4][CH2:3][OH:2])[CH:7]=2)[N:12]=[CH:11][N:10]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 69259874HCID 69259874, Verbindung

Produkt 1

HCID 694856033-(4-Phenoxy-quinazolin-6-yl)-prop-2-en-1-olAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ester 24 (1.35 g, 4.41 mmol) in toluene (60 mL) under N2 at −78° C. was added DIBAL-H (8.8 mL of a 1M solution in toluene, 8.8 mmol) dropwise. The reaction was then warmed to 0° C. and stirred for 30 minutes, then quenched with 30 mL of saturated Rochelle's salt and the mixture stirred overnight. The bilayer was transferred to a separatory funnel and the organic layer washed with H2O and brine and dried (MgSO4). After filtration the organic layer was concentrated under reduced pressure to provide a yellow oil which was purified by silica gel chromatography eluting with 1:1 hexanes:EtOAc, then EtOAc. The allylic alcohol 25 (900 mg, 73%) was isolated as a pale yellow oil. 1H NMR (CDCl3; 400 MHz): δ: 8.72 (s, 1 H), 8.27 (s, 1H), 7.66 (m, 2H), 7.62 (m, 1H), 7.47 (m, 3H), 7.34 (m, 1H), 7.24 (m, 2H), 6.82 (dd, 1h), 6.56 (m, 1H), 4.41 (dd, 1H).

Aufarbeitung

  1. customquenched with 30 mL of saturated Rochelle's salt
  2. stirringthe mixture stirred overnight
  3. customThe bilayer was transferred to a separatory funnel
  4. washthe organic layer washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. filtrationAfter filtration the organic layer
  7. concentrationwas concentrated under reduced pressure
  8. customto provide a yellow oil which
  9. customwas purified by silica gel chromatography
  10. washeluting with 1:1 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3a8c27ca7c534e3bbfa515ddfa1efb59
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541481B2

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