Bis(2-pyridyl) ketone → 2-Heptenoic acid

HRID 378741

Reaktionsgleichung

Reaktionsgleichung von HRID 378741
N1C=C[CH:4]=[CH:3][C:2]=1[C:7]([C:9]1C=CC=CN=1)=O.CO.[CH3:17][C:18]([OH:20])=[O:19].C(Cl)Cl>>[C:18]([OH:20])(=[O:19])/[CH:17]=[CH:4]/[CH2:3][CH2:2][CH2:7][CH3:9]

Komponenten

3

Edukt 2

HCID 88065Bis(2-pyridyl) ketoneHCID 21877243DCM MeOH AcOH

Produkt 1

HCID 52827092-Heptenoic acidAusbeute 70 %

Versuchsvorschrift

Prepared as above from 376.4 mg (0.86 mmol) of the (±)-pyridyl ketone and 790.6 mg (1.73 mmol) of the Wittig salt. Preparative HPLC with MeOH-AcOH-CH2Cl2 (4:1:95) gave in ~92% yield a mixture of Wittig product (E/Z=~96:4) from which 320.9 mg (70%) of (±)-(E)-heptenoic acid was isolated cleanly: mp 68-73° C.; 1H NMR (CDCl3) δ8.61 (br s, 1H), 8.49 (br s, 1H), 8.28 (s, 1H), 8.06 (d, J=8.1 Hz, 2H), 7.52 (br s, 1H), 7.46 (br d, J=8.0 Hz, 1H), 7.28 (d, 2H), 7.27 (buried, 1H), 6.21 (t, J=7.4 Hz, 1H), 4.04 (dt, J=13.3, 1.9 Hz, 1H), 3.69 (br s, 4H), 3.50 (m, 5H), 2.33 (dd, J=7.1, 6.7 Hz, 2H), 2.21 (ddd, J=7.2, 7.0, 6.7 Hz, 2H), 1.89-1.26 (m, 10H); FDMS 534 (M+1). Anal. (C30H35N3O6.0.25C2H4O2) C, H, N.

Quellen und Nachweise

ORD-Eintrag
ord-d4090b9a4a10460fbf67a55496b5811a
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06031095

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