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

HRID 2289576ノート

反応式

HRID 2289576 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒4 回

反応条件

温度
-58 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-4110a909f8b34625b996745238c8e886
出典データセット
uspto-grants-2000_07
特許番号
US06093714

反応ノート

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