Triethylamine → 3-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one

HRID 459775

反応式

HRID 459775 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4](P(=O)(OC)OC)[O:3]1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27].C(N(CC)CC)C>O1CCCC1>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2](=[O:1])[O:3]2)=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 855054-Chloro-3-nitrobenzaldehydeHCID 11118213Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

生成物 1

HCID 686228163-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
15 °C

実験手順

A stirred solution of dimethyl 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonate (4.84 g, 0.02 mol; prepared in a manner similar to that described in Example 23) and 4-chloro-3-nitrobenzaldehyde (3.71 g, 0.02 mol) in tetrahydrofuran (30 ml) was cooled to 15° C. and a solution of triethylamine (2.02 g, 0.02 mol) in tetrahydrofuran (3 ml) was added dropwise at <25° C. The mixture was stirred at ambient temperature for 1 hour, allowed to stand at this temperature for a further 16 hours and the resulting solid was collected by filtration. The filtrate was concentrated in vacuo, the residue was triturated with water (5 ml) and the resulting solid was collected by filtration. The two crops of solid were combined and suspended in water (30 ml). The mixture was stirred at ambient temperature for 30 minutes and the resulting solid was collected by filtration and dried in vacuo for 24 hours to give crude 3-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one as a pale yellow solid, m.pt. 198–204° C., still slightly wet with water, which was used directly in the next stage.

後処理

  1. customprepared in a manner similar to
  2. waitto stand at this temperature for a further 16 hours
  3. filtrationthe resulting solid was collected by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was triturated with water (5 ml)
  6. filtrationthe resulting solid was collected by filtration
  7. stirringThe mixture was stirred at ambient temperature for 30 minutes
  8. filtrationthe resulting solid was collected by filtration
  9. customdried in vacuo for 24 hours

出典と根拠

ORDレコード
ord-eef7148da5474d7cb8dcb63a22b909da
出典データセット
uspto-grants-2007_03
特許番号
US07196085B2

関連ノート

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