Propargyl alcohol → 3-(4-Nitrophenyl)prop-2-yn-1-ol

HRID 24931

반응식

HRID 24931 반응식
[CH2:1]([OH:4])[C:2]#[CH:3].C(N(CC)CC)C.Br[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1>C(#N)C.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].[Cu]I>[OH:4][CH2:1][C:2]#[C:3][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1

참가 물질

8

반응물 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 114661-Bromo-4-nitrobenzene

생성물 1

HCID 50337133-(4-Nitrophenyl)prop-2-yn-1-ol

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

8.55 g (0.15 mol) of propargyl alcohol and 152 ml (110 g, 1.09 mol) of triethylamine are added to a solution of 20.2 g (0.1 mol) of 4-bromonitrobenzene in 285 ml of acetonitrile. The reaction solution is heated to 100° C. 11.9 g (10 mmol) of Pd(Pph3)4 and 3.94 g (20 mmol) of copper (I) iodide are added. After 10 minutes the solvent is eliminated in vacuo and the residue taken up in ethyl acetate. It is washed with water and ammonia water, filtered through Celite and the solvent is eliminated in vacuo. The product is obtained by chromatography on silica gel (dichloromethane/methanol=10:1).

후처리

  1. washIt is washed with water and ammonia water
  2. filtrationfiltered through Celite
  3. customThe product is obtained by chromatography on silica gel (dichloromethane/methanol=10:1)

출처 및 근거

ORD 기록
ord-7d8c42409bc3412a8e79172bc76b0462
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855710B2

연결된 노트

불러오는 중…