Phosphorus tribromide → benzyl 2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate

HRID 377573ノート

反応式

HRID 377573 の反応式
P(Br)(Br)[Br:2].O[CH2:6][C:7]1[O:12][CH2:11][N:10]([C:13]([CH3:25])([CH3:24])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C:9](=[O:26])[C:8]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCOCC.O1CCCC1>[Br:2][CH2:6][C:7]1[O:12][CH2:11][N:10]([C:13]([CH3:25])([CH3:24])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C:9](=[O:26])[C:8]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

5

反応物 2

HCID 24614Phosphorus tribromideHCID 19354618benzyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate

生成物 1

HCID 19354577benzyl 2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

A solution of phosphorus tribromide (5.1 ml) in ether was added during 0.5 hour to a solution of benzyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (61.1 g) in a mixture of ether and tetrahydrofuran at -78° C. The mixture was then stirred at -10° C. for 4 hours and at room temperature for 1 hour, then washed (water), dried (magnesium sulphate) and evaporated. Purification of the residue by dry column chromatography on silica gel gave benzyl 2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (46.1 g), NMR(CDCl3) 1.5(s,6H), 3.8(s,2H), 5.05(s,2H), 5.3(s,2H), 7.2(s,5H).

後処理

  1. washwashed (water)
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated
  4. customPurification of the residue
  5. customby dry column chromatography on silica gel

出典と根拠

ORDレコード
ord-e332b796c361411c81b06dd2545753c7
出典データセット
uspto-grants-2000_02
特許番号
US06028032

反応ノート

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