Decalin → N-[1-(Benzyloxy)but-3-en-2-yl]-2,2,2-trichloroacetamide

HRID 595326ノート

反応式

HRID 595326 の反応式
[H-].[Na+].[CH2:3]([O:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:16][C:17]([Cl:21])([Cl:20])[C:18]#[N:19].C1C2C(CCCC2)CCC1.C1C[O:35]CC1>O>[CH2:3]([O:10][CH2:11][CH:12]([NH:19][C:18](=[O:35])[C:17]([Cl:21])([Cl:20])[Cl:16])[CH:13]=[CH2:14])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

7

反応物 5

HCID 7044DecalinHCID 8028TetrahydrofuranHCID 11011TrichloroacetonitrileHCID 24758Sodium hydrideHCID 11008492cis-4-Benzyloxy-2-buten-1-ol

生成物 1

HCID 13416079N-[1-(Benzyloxy)but-3-en-2-yl]-2,2,2-trichloroacetamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Sodium hydride (53 mg, 2.4 mmol) was added to a solution of (2Z)-4-(benzyloxy)but-2-en-1-ol (2.0 g, 11 mmol) in THF (50 mL) at 0° C. 2,2,2-trichloroacetonitrile (1.63 g, 12 mmol) was added dropwise to the reaction mixture at 0° C. over a period of 30 minutes. The reaction mixture was stirred at room temperature for an additional 2 hours. The reaction mixture was concentrated under reduced pressure and then diluted with decahydronaphthalene (35.8 g, 259 mmol). The mixture was stirred and heated to 200° C. for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give N-[1-(benzyloxy)but-3-en-2-yl]-2,2,2-trichloroacetamide. 1H NMR (400 MHz, CDCl3) δ 7.38-7.11 (m, 6H), 5.93-5.86 (m, 1H), 5.34-5.27 (m, 2H), 4.60-4.58 (m, 3H), 3.66-3.61 (m, 2H).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringThe mixture was stirred
  3. temperatureheated to 200° C. for 5 hours
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford the crude product residue
  10. customThe crude product residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-ec8200a459774c83a205477e739fd847
出典データセット
uspto-grants-2016_01
特許番号
US09242984B2

反応ノート

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