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

HRID 440950

反応式

HRID 440950 の反応式
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

参加物

6

反応物 2

HCID 70041-IodonaphthaleneHCID 793464-Pentyn-1-ol2 回

生成物 1

HCID 199555575-(1-Naphthyl)-4-pentyn-1-ol収率 68.7%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8021Diethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0e2091d86477426185264f1752389d97
出典データセット
uspto-grants-1996_05
特許番号
US05521192

関連ノート

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