1-Iodonaphthalene → 5-(1-Naphthyl)-4-pentyn-1-ol

HRID 440950

반응식

HRID 440950 반응식
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:12]([OH:17])[CH2:13][CH2:14][C:15]#[CH:16]>C(NCC)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>[C:2]1([C:16]#[C:15][CH2:14][CH2:13][CH2:12][OH:17])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 2

HCID 70041-IodonaphthaleneHCID 793464-Pentyn-1-ol2회

생성물 1

HCID 199555575-(1-Naphthyl)-4-pentyn-1-ol수율 68.7%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8021Diethylamine용매

실험 절차

Under a nitrogen atmosphere, a mixture of 4.0 mL (0.027 mole) of 1-iodonaphthalene, 0.1 gram (0.0003 mole) of copper(I) iodide, and 0.19 gram (0.0003 mole) of bis(triphenylphosphine)palladium(II) chloride in 75 mL of diethylamine was stirred, and 2.6 mL (0.027 mole) of 4-pentyn-1-ol was added in one portion. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 18 hours. Gas chromatographic (GC) analysis of the reaction mixture indicated that the reaction had not gone to completion. An additional 0.5 mL of the 4-pentyn-1-ol was added, and the reaction mixture was stirred for an additional six hours. GC analysis of the reaction mixture indicated that the reaction was complete. The reaction mixture was passed through a column of silica gel. Elution was accomplished using methylene chloride. The eluate was concentrated under reduced pressure, yielding 3.9 grams of 5-(naphth-1-yl)-4-pentyn-1-ol. The NMR spectrum was consistent with the proposed structure.

후처리

  1. additionUpon completion of addition
  2. stirringthe reaction mixture was stirred at ambient temperature for about 18 hours
  3. stirringthe reaction mixture was stirred for an additional six hours
  4. washElution
  5. concentrationThe eluate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0e2091d86477426185264f1752389d97
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521192

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