3-Butyn-1-OL → N-[4-formyl-2-(4-hydroxy-but-1-ynyl)-phenyl]-acetamide

HRID 591680ノート

反応式

HRID 591680 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[C:5](I)[CH:4]=1)=[O:2].[CH2:14]([OH:18])[CH2:15][C:16]#[CH:17]>CN(C=O)C.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[C:5]([C:17]#[C:16][CH2:15][CH2:14][OH:18])[CH:4]=1)=[O:2]

参加物

7

反応物 2

HCID 135663-Butyn-1-OLHCID 229919464-Acetamido-3-iodobenzaldehyde

生成物 1

HCID 86662028N-[4-formyl-2-(4-hydroxy-but-1-ynyl)-phenyl]-acetamide

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒2 回HCID 8471Triethylamine溶媒2 回

反応条件

温度
80 °C

実験手順

To a degassed solution of N-(4-formyl-2-iodo-phenyl)-acetamide (0.810 g, 2.82 mmol) in DMF (25 mL) and triethylamine (5 mL) were added PdCl2(PPh3)2 (0.10 g, 0.14 mmol) and copper (I) iodide (0.16 g, 0.85 mmol). A degassed solution of but-3-yn-1-ol (0.27 g, 0.29 mmol) in DMF (8 mL) and triethylamine (2 mL) was added at 80° C. over a period of 1 hour under nitrogen. After the addition, the reaction mixture was stirred at 80° C. for 4 hours, cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with water (100 mL) and extracted with ethyl acetate (200 mL). The organic phase was washed with brine (100 mL) and dried over anhydrous Na2SO4. Removal of solvent gave N-[4-formyl-2-(4-hydroxy-but-1-ynyl)-phenyl]-acetamide as a brown solid. Crude yield: 0.85 g (100%). The crude material was used in next step without further purification.

後処理

  1. additionAfter the addition
  2. temperaturecooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with water (100 mL)
  5. extractionextracted with ethyl acetate (200 mL)
  6. washThe organic phase was washed with brine (100 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. customRemoval of solvent

出典と根拠

ORDレコード
ord-1dfd0c9d8ca642598fc46de7d3ea8380
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

反応ノート

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