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

HRID 395375

반응식

HRID 395375 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6344Dichloromethane용매HCID 8021Diethylamine용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-929d5a52771a4fb78e7fade0ed26344a
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605628B1

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