Acetic Acid → 2-[2-(2-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-hydroxy-ethoxy)-phenyl]-propan-2-ol

HRID 512920ノート

反応式

HRID 512920 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]4[CH2:22][O:21]4)[CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1.[OH:23][C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33])([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CN(C=O)C.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:20]([OH:21])[CH2:22][O:33][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[C:24]([OH:23])([CH3:26])[CH3:25])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 8279552-(2-Hydroxypropan-2-yl)phenolHCID 867207317-Chloro-2-[(E)-2-(3-oxiranyl-phenyl)-vinyl]-quinoline

生成物 1

HCID 867207322-[2-(2-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-hydroxy-ethoxy)-phenyl]-propan-2-ol収率 46.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
125 °C

実験手順

To a stirred solution of epoxide 30 (10.0 g, 32.57 mmol) in DMF (30 ml) was added alcohol 31 (7.425 g, 48.85 mmol), potassium carbonate (8.99 g, 65.14 mmol). The reaction mixture was stirred overnight at 120-130° C. The resulted mixture was treated with 10% aq. acetic acid, diluted further with water followed by usual workup in ethyl acetate and FC to give diol 32 (7.0 g, 46%).

出典と根拠

ORDレコード
ord-b93abc29ee7a4ad08b3fb18378423ee9
出典データセット
uspto-grants-2015_08
特許番号
US09102665B2

反応ノート

読み込み中…