Triethylamine → 1-(2-Cyclopropylethynyl)-4-methoxybenzene

HRID 45275

反応式

HRID 45275 の反応式
C1(C#C)CC1.[CH:6]1([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:8][CH2:7]1.IC1C=CC(OC)=CC=1.C(N(CC)CC)C>O1CCCC1.[Cu]I>[CH:6]1([C:9]#[C:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH2:8][CH2:7]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 696764-IodoanisoleHCID 866035461-Cyclopropylethynyl-4-methoxy-benzene Cyclopropylethyne

生成物 1

HCID 586098031-(2-Cyclopropylethynyl)-4-methoxybenzene収率 67%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

1-Cyclopropylethynyl-4-methoxy-benzene Cyclopropylethyne (15 g, 0.22 mol) was slowly added to a mixture of 4-iodoanisole (30 g, 0.13 mol), copper (I) iodide (1.2 g, 0.0063 mol), and triethylamine (30 g, 0.30 mol) in tetrahydrofuran (THF, 400 mL). After being stirred for 4 hours, the resulting precipitate was filtered and washed with THF. The combined filtrate was evaporated to dryness and the residue was purified by column chromatography to afford 1-cyclopropylethynyl-4-methoxy-benzene as a yellow oil (15 g, 0.087 mol, 67%). NMR (CDCl3) δ 7.31 (d, J=8.8 Hz, 2 H), 6.80 (d, J=8.8 Hz, 2H), 3.79 (s, 3H), 1.43 (m, 1H), 0.85 (m, 2H), 0.78 (m, 2H).

後処理

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with THF
  3. customThe combined filtrate was evaporated to dryness
  4. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-9a5a8d6383894334bbc0af4ce4de09ce
出典データセット
uspto-grants-2013_09
特許番号
US08541453B2

関連ノート

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