Ethyl propiolate → Ethyl 4-hydroxy-4-(3,4,5-trimethoxy-2-nitrophenyl)-2-butynoate

HRID 2289576노트

반응식

HRID 2289576 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[C:12]#[CH:13].[CH3:18][O:19][C:20]1[C:21]([N+:32]([O-:34])=[O:33])=[C:22]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH:23]=[O:24]>O1CCCC1>[OH:24][CH:23]([C:22]1[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:20]([O:19][CH3:18])[C:21]=1[N+:32]([O-:34])=[O:33])[C:13]#[C:12][C:11]([O:15][CH2:16][CH3:17])=[O:14]

참가 물질

5

반응물 3

HCID 12182Ethyl propiolateHCID 2733832Lithium HexamethyldisilazideHCID 186979183,4,5-Trimethoxy-2-nitrobenzaldehyde

생성물 1

HCID 18697795Ethyl 4-hydroxy-4-(3,4,5-trimethoxy-2-nitrophenyl)-2-butynoate수율 68.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매4회

반응 조건

온도
-58 °C

실험 절차

A 1.0 M solution (1.9 ml) of lithium bistrimethylsilylamide in tetrahydrofuran was added to tetrahydrofuran (4.0 ml) at -78° C. under an argon atmosphere, and the mixture was stirred for 30 min. A solution of ethyl propiolate (176 μl, 1.74 mmol) in tetrahydrofuran (1.0 ml) was added thereto, and the mixture was stirred for 30 min. A solution of 3,4,5-trimethoxy-2-nitrobenzaldehyde (280 mg, 1.16 mmol), prepared in the step (b), in tetrahydrofuran (2.5 ml) was added thereto, and the temperature was raised to -58° C., followed by stirring for 30 min. The reaction mixture was poured into an ice-cold 10% aqueous ammonium chloride solution, and the mixture was vigorously stirred for 5 min. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give ethyl 4-hydroxy-4-(3,4,5-trimethoxy-2-nitrophenyl)-2-butynoate as an oil (268 mg, 68%).

후처리

  1. stirringthe mixture was stirred for 30 min
  2. additionwas added
  3. stirringby stirring for 30 min
  4. stirringthe mixture was vigorously stirred for 5 min
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-4110a909f8b34625b996745238c8e886
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06093714

반응 노트

불러오는 중…