Acetic Acid → HCID 86588959, 화합물

HRID 353305

반응식

HRID 353305 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

HCID 86588959HCID 86588959, 화합물수율 15.9%

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9bf7cf013c9346a6ba84e0b6b4b2f77f
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750252B2

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