Hydrochloric Acid → 4,4-Diethoxy-1-(4-nitrophenyl)but-2-yn-1-one

HRID 456791

반응식

HRID 456791 반응식
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[CH:6])[CH3:2].[Li]CCCC.CON(C)[C:18](=[O:28])[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.Cl>C1COCC1>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[C:6][C:18]([C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)=[O:28])[CH3:2]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 662853,3-DiethoxypropyneHCID 2991007N-methoxy-N-methyl-4-nitrobenzamide2회HCID 178418339Butyllithium

생성물 1

HCID 184385944,4-Diethoxy-1-(4-nitrophenyl)but-2-yn-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

3,3-Diethoxyprop-1-yne (8.5 ml, 59 mmol) was dissolved in THF (100 ml). The solution was cooled to −70° C., and nBuLi (19 ml of 2.5 M soln in hexanes, 47.5 mmol) was added over 5 min. The solution was warmed to 0° C. for 15 min, then cooled to −70 ° C. again. A solution of N-methoxy-N-methyl-4-nitrobenzamide (Intermediate 8, 8.04 g, 38.1 mmol) in THF (50 ml) was added dropwise over 15 min. The solution was warmed to 0° C. after 15 min, and held there for 45 min. The reaction mixture was poured into 1M HCl, extracted with ethyl acetate and dried over sodium sulfate. Purification by chromatography on silica gel eluting with 30 to 50% dichloromethane: hexane, gave the title compound as a light orange oil which solidified on standing (7.14 g).

후처리

  1. temperatureThe solution was warmed to 0° C. for 15 min
  2. temperaturecooled to −70 ° C. again
  3. temperatureThe solution was warmed to 0° C. after 15 min
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. customPurification by chromatography on silica gel eluting with 30 to 50% dichloromethane

출처 및 근거

ORD 기록
ord-52ad3e59f4f24aa3a7736f9b578531f6
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186738B2

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