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

HRID 456791

反応式

HRID 456791 の反応式
[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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 662853,3-DiethoxypropyneHCID 2991007N-methoxy-N-methyl-4-nitrobenzamide2 回HCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-52ad3e59f4f24aa3a7736f9b578531f6
出典データセット
uspto-grants-2007_03
特許番号
US07186738B2

関連ノート

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