Water → ethyl(2E)-3-(1,2,3-benzothiadiazol-7-yl)acrylate

HRID 1639845ノート

反応式

HRID 1639845 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[S:17]1[C:21]2[C:22]([CH:26]=O)=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1.O>O1CCCC1>[S:17]1[C:21]2[C:22](/[CH:26]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1

参加物

6

反応物 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 14835681Benzo[d][1,2,3]thiadiazole-7-carbaldehyde

生成物 1

HCID 66720648ethyl(2E)-3-(1,2,3-benzothiadiazol-7-yl)acrylate収率 98.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a suspension of 55% sodium hydride (1.81 g, 41.5 mmol) in tetrahydrofuran (30 mL) was added a solution of ethyl diethylphosphonoacetate (8.31 mL, 41.5 mmol) in tetrahydrofuran (10 mL) at 0° C. and the mixture was stirred for 20 min. To the reaction mixture was added a solution of 1,2,3-benzothiadiazole-7-carbaldehyde (6.20 g, 37.8 mmol) in tetrahydrofuran (60 mL) at 0° C. and the mixture was stirred at room temperature for 4 hr. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) and recrystallization (ethyl acetate/hexane) to give the title compound (8.70 g, yield 98%).

後処理

  1. stirringthe mixture was stirred at room temperature for 4 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) and recrystallization (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-4b0a602c34f14e11b86034dc0869918a
出典データセット
uspto-grants-2012_02
特許番号
US08110585B2

反応ノート

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