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

HRID 378744

반응식

HRID 378744 반응식
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]

참가 물질

3

반응물 2

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

생성물 1

HCID 52827092-Heptenoic acid수율 46%

실험 절차

Prepared as above from 165.4 mg (0.44 mmol) of the pyridyl ketone and 395.6 mg (0.87 mmol) of the Wittig salt. Preparative HPLC with MeOH-AcOH-CH2Cl2 (2:1:97) furnished 94.8 mg (46%) of the pure (E)-heptenoic acid: mp 67-72° C.; 1H NMR (CDCl3) δ8.60 (s, 1H), 8.48 (br s, 1H), 8.25 (s, 1H), 8.05 (d, J=8.2 Hz, 2H), 7.62 (distorted t, J=~5.3 Hz, 1H), 7.43 (br d, J=7.8 Hz, 1H), 7.28 (buried, 1H), 7.26 (d, 2H), 6.22 (t, J=7.4 Hz, 1H), 3.50 (m, 6H), 2.30 (ddd, J=7.1, 7.1, 6.9 Hz, 2H), 2.20 (ddd, J=7.6, 7.2, 6.9 Hz, 2H), 1.90 (tt, J=6.1, 6.1 Hz, 2H), 1.64-1.54 (m, 4H), 1.28 (t, J=7.0 Hz, 3H); FDMS 478 (M+1). Anal. (C27H31N3O5.0.6CH4O.0.8H2O) C, H, N.

출처 및 근거

ORD 기록
ord-ce7a00d60deb48bd8d44e24ce3d0ca8e
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06031095

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