Triethylamine → 3-{[4-(Methoxymethoxy)phenyl]ethynyl}-4-formylthiophene

HRID 1251169ノート

反応式

HRID 1251169 の反応式
[CH:1]([C:3]1[C:7](Br)=[CH:6][S:5][CH:4]=1)=[O:2].C(N(CC)CC)C.[CH3:16][O:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[CH:27])=[CH:22][CH:21]=1>CN(C=O)C.[Cu]I.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>[CH3:16][O:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][C:7]2[C:3]([CH:1]=[O:2])=[CH:4][S:5][CH:6]=2)=[CH:22][CH:21]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 27642074-Bromothiophene-3-carboxaldehydeHCID 225029951-Ethynyl-4-(methoxymethoxy)benzene

生成物 1

HCID 225030313-{[4-(Methoxymethoxy)phenyl]ethynyl}-4-formylthiophene収率 66.9%

試薬・触媒・溶媒 3

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

実験手順

3-Formyl-4-bromothiophene (14.7 g) was dissolved in DMF (100 ml), followed by the addition of triethylamine (100 ml), CuI (0.25 g), Pd(PPh3)2Cl2 (0.5 g) and 4-methoxymethoxy-1-ethynylbenzene (11.4 g), and the mixture was reacted at 70° C. overnight. The reaction solution was filtered through Celite, poured into 1N hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with an aqueous solution of saturated sodium bicarbonate and brine, dried and evaporated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system), to give 3-{[4-(methoxymethoxy)phenyl]ethynyl}-4-formylthiophene as a colorless oil (12.8 g, yield; 47%).

後処理

  1. customthe mixture was reacted at 70° C. overnight
  2. filtrationThe reaction solution was filtered through Celite
  3. additionpoured into 1N hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous solution of saturated sodium bicarbonate and brine
  6. customdried
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

出典と根拠

ORDレコード
ord-63b633c7431a4c6e9c8caa428c0413c2
出典データセット
uspto-grants-2002_01
特許番号
US06340759B1

反応ノート

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