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

HRID 512920노트

반응식

HRID 512920 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
125 °C

실험 절차

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%).

출처 및 근거

ORD 기록
ord-b93abc29ee7a4ad08b3fb18378423ee9
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102665B2

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