Benzaldehyde → Benzaldehyde-O-(2-carboxyphenyl)oxime

反応式

C(=O)[C:2]1[CH:7]=[CH:6]C=[CH:4][CH:3]=1.C(O[C:12](=[N:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([OH:24])=[O:23])[CH3:13])C>>[C:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][N:14]=[CH:12][C:13]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)([OH:24])=[O:23]

参加物

反応物 2

HCID 240Benzaldehyde

HCID 72810275Ethyl-N-(2-carboxyphenoxy)acetimidate

生成物 1

HCID 72828820Benzaldehyde-O-(2-carboxyphenyl)oxime収率 62%

実験手順

70% HClO4 (14.0 μL, 0.163 mmol), benzaldehyde (18.0 mL, 0.177 mmol), and 20 (39.0 mg, 0.175 mmol) were subjected to the representative coupling procedure as outlined above (method 3), yielding 2a as a white solid (26.1 mg, 62%). 1H-NMR (500 MHz, d6-Acetone) δ 7.15 (dt, J=0.9, 7.8 Hz, 1H), 7.48-7.55 (m, 3H), 7.59 (dt, J=1.8, 7.8 Hz, 1H), 7.71 (d, J=8.2 Hz, 1H), 7.83-7.89 (m, 3H), 8.66 (s, 1H), 10.8-11.5 (broad s, 1H); 13C-NMR (125 MHz, d6-DMSO) δ 115.7, 119.7, 122.1, 127.8, 129.0, 130.8, 130.9, 131.1, 133.1, 153.4, 157.7, 166.8; MALDI-FTMS (DHB) 242.0811 m/z [MH]+, C14H12NO3 requires 242.0812. RP-HPLC: >99% pure.

出典と根拠

ORDレコード: ord-5254e110cd1246f5b3a5b12e429d7878
出典データセット: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07312361B2

反応ノート

読み込み中…