Pyridine → Chloro-oxo-acetic acid 2-oxo-3-phenyl-2,3-dihydro-benzofuran-5-yl ester

HRID 55561

반응식

HRID 55561 반응식
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=[O:3].N1C=CC=CC=1.[OH:13][C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20](=[O:22])[CH:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:18]=2[CH:29]=1>ClCCl>[O:22]=[C:20]1[CH:19]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:18]2[CH:29]=[C:14]([O:13][C:1](=[O:5])[C:2]([Cl:4])=[O:3])[CH:15]=[CH:16][C:17]=2[O:21]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 106329835-hydroxy-3-phenyl-3H-benzofuran-2-one

생성물 1

HCID 53805502Chloro-oxo-acetic acid 2-oxo-3-phenyl-2,3-dihydro-benzofuran-5-yl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Oxalyl chloride (17.5 parts) and pyridine (0.5 parts) were added to a suspension of 5-hydroxy-2-oxo-3-phenyl-2,3-dihydrobenzfuran (22.6 parts) in dichloromethane (200 parts). After six hours reflux, chloro-oxo-acetic acid 2-oxo-3-phenyl-2,3-dihydro-benzofuran-5-yl ester was isolated and phenol (9.9 parts) added and the mixture refluxed for eighteen hours. Removal of the solvent gave the crude product oxalic acid (2-oxo-3-phenyl-2,3-dihydro-benzofuran-5-yl)ester phenyl ester (33.3 parts; 89%). Trituration in methanol and recrystallisation from ethyl acetate gave a pure product. Analysis C,70.4; H,3.7; C22H13O6 requires C,70.8; H,3.5%. M.pt.134° C., 1H and 13Cnmr gave spectra consistent with structure.

후처리

  1. temperatureAfter six hours reflux

출처 및 근거

ORD 기록
ord-bd493e39dd8a4bbd9af7024a9ad73ed1
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05625080

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