Acetic Acid → HCID 86588959、化合物

HRID 353305ノート

反応式

HRID 353305 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:21].CC(C)([O-])C.[K+].C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1.C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[C:23](\[O:22][CH2:20][CH3:21])/[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 5

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 69955Ethyl ethoxyacetateHCID 70235544-(Benzyloxy)-3-nitrobenzaldehydeHCID 23665647Potassium tert-butoxide

生成物 1

HCID 86588959HCID 86588959、化合物収率 15.9%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

4-(Benzyloxy)-3-nitrobenzaldehyde (4.12 g; 14.4 mmole) and ethyl ethoxyacetate (2.29 g; 17.3 mmole) were dissolved in dry tetrahydrofuran (20 ml) and cooled to −20° C. Potassium tert-butoxide (1.94 g; 17.3 mmole) dissolved in dry tetrahydrofuran (10 ml) was slowly added and the reaction was stirred overnight at −20° C. The reaction was quenched with acetic acid (1.3 g; 21.7 mmole). The crude product was isolated, redissolved in toluene and refluxed over night with p-toluenesulfonic acid (0.25 g; 1.44 mmole) in a Dean-Stark apparatus to separate the water. The solution was cooled, washed with sodium hydrogen carbonate, dried with magnesium sulfate and evaporated. Chromatography of the crude material from methylene chloride gave 0.85 g (11% yield) of ethyl (2Z)-3-[4-(benzyloxy)-3-nitrophenyl]-2-ethoxyacrylate.

後処理

  1. additionwas slowly added
  2. customThe crude product was isolated
  3. customto separate the water
  4. temperatureThe solution was cooled
  5. washwashed with sodium hydrogen carbonate
  6. dry with materialdried with magnesium sulfate
  7. customevaporated

出典と根拠

ORDレコード
ord-9bf7cf013c9346a6ba84e0b6b4b2f77f
出典データセット
uspto-grants-2004_06
特許番号
US06750252B2

反応ノート

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