4-Pentyn-1-ol → 5-(2,5-Dichlorophenyl)pent-4-yn-1-ol

HRID 395375

反応式

HRID 395375 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1I.[CH2:10]([OH:15])[CH2:11][CH2:12][C:13]#[CH:14]>C(NCC)C.ClCCl.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:14]#[C:13][CH2:12][CH2:11][CH2:10][OH:15]

参加物

6

反応物 2

HCID 793464-Pentyn-1-olHCID 1224521,4-Dichloro-2-iodobenzene

生成物 1

HCID 223207595-(2,5-Dichlorophenyl)pent-4-yn-1-ol

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6344Dichloromethane溶媒HCID 8021Diethylamine溶媒

実験手順

A solution of 1,4-dichloro-2-iodobenzene (20.0 g, 73.3 mmol), 4-pentyn-1-ol (6.17 g, 73.3 mmol), bistriphenylphosphine(Pd II) chloride (1.03 g, 1.47 mmol), and copper(I) iodide (0.14 g, 0.733 mmol) in 400 ml of diethylamine was stirred under nitrogen for three days. This was diluted with dichloromethane and the oily layer was adsorbed onto silica gel and eluted with hexanes-ethyl acetate (5:1) to give 5-(2,5-dichlorophenyl)pent-4-yn-1-ol, 13.7 g (82%); NMR (CDCl3) δ 1.9 (m, 2H), 2.6 (t, 2H), 3.85 (t, 2H), 7.2 (dd, 1H), 7.28 (m, 1H), 7.4 (d, 2H).

後処理

  1. washeluted with hexanes-ethyl acetate (5:1)

出典と根拠

ORDレコード
ord-929d5a52771a4fb78e7fade0ed26344a
出典データセット
uspto-grants-2003_08
特許番号
US06605628B1

関連ノート

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