2-Chloromethyl 2-(trimethylsilyl)ethyl ether → 8-nitroquinoxalin-2(1H)-one

HRID 132546ノート

反応式

HRID 132546 の反応式
C[Si](C)(C)[CH2:3][CH2:4][O:5]CCl.[N+:10]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[N:15]=CC(=O)[NH:18]2)([O-:12])=[O:11]>O1CCCC1>[N+:10]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[NH:15][C:4](=[O:5])[CH:3]=[N:18]2)([O-:12])=[O:11]

参加物

4

反応物 2

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 113445095-nitroquinoxalin-2-one

生成物 1

HCID 6406068-nitroquinoxalin-2(1H)-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Chloromethyl 2-(trimethylsilyl)ethyl ether (10.0 mL, 56.3 mmol) was added to tetrahydrofuran solution (500 mL) containing a mixture (21.6 g) of the 5-nitroquinoxalin-2-one derivative and the 8-nitroquinoxalin-2-one derivative obtained in the above (1), and then sodium hydride (2.30 g, 60% dispersion in oil, 57.3 mmol) was added thereto under ice-cooling. After the resulting reaction solution was stirred at room temperature for 1.5 hours, aqueous ammonium chloride solution was added thereto, and the mixture was extracted with chloroform. After the organic layer was washed with saturated brine, it was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. To the resulting residue was added 4N hydrogen chloride/1,4-dioxane solution (100 mL), and the solution was stirred at room temperature for 1 hour. After removal of the insolubles by filtration, the filtrate was concentrated in vacuo. The resulting residue was purified by a column chromatography on silica gel to obtain the above 5-nitroquinoxaline-2-one derivative (11.6 g) protected with SEM, as a yellow solid.

出典と根拠

ORDレコード
ord-f0981b475bb64dbfab0ad6e903d7bd38
出典データセット
uspto-grants-2008_06
特許番号
US07388010B2

反応ノート

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