Water → 6-(2-Bromoacetyl)-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17345ノート

反応式

HRID 17345 の反応式
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:21]#[N:22])[C:10]([CH3:20])=[C:11]([C:15]([O:17]CC)=[CH2:16])[C:12]=3[O:13][CH3:14])[N:8]=2)[CH2:3][CH2:2]1.O.[Br:24]N1C(=O)CCC1=O>O1CCCC1>[Br:24][CH2:17][C:15]([C:11]1[C:12]([O:13][CH3:14])=[C:6]2[O:5][C:4]([CH:1]3[CH2:3][CH2:2]3)=[N:8][C:7]2=[C:9]([C:21]#[N:22])[C:10]=1[CH3:20])=[O:16]

参加物

5

反応物 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 68586975HCID 68586975、化合物

生成物 1

HCID 866308376-(2-Bromoacetyl)-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile収率 81.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile (I-84) (2.58 g, 8.46 mmol) was dissolved in tetrahydrofuran (130 ml), water (7.7 ml) and N-bromosuccinimide (1.61 g, 8.89 mmol) were added all at a time, followed by stirring at room temperature for 1.5 hours. After the reaction, the solvent was evaporated away under reduced pressure, followed by dilution with ethyl acetate and by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography (covering) and eluted with a mixed solvent of n-hexane/ethyl acetate (2:1, v/v) to obtain the entitled compound (2.40 g, 81%) as a yellow white solid.

後処理

  1. customAfter the reaction
  2. customthe solvent was evaporated away under reduced pressure
  3. washby washing with water and saturated brine
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. washeluted with a mixed solvent of n-hexane/ethyl acetate (2:1

出典と根拠

ORDレコード
ord-8c7f0e59410842f6a5c9846b05f992ab
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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