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

HRID 1464595ノート

反応式

HRID 1464595 の反応式
C(NCC)C.[CH2:6]([OH:9])[C:7]#[CH:8].I[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1>O1CCCC1.O.[Cu]I.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]>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]#[C:7][CH2:6][OH:9])=[CH:12][CH:13]=1

参加物

8

反応物 3

HCID 7859Propargyl alcoholHCID 8021DiethylamineHCID 696764-Iodoanisole

生成物 1

HCID 120031913-(4-methoxyphenyl)prop-2-yn-1-ol収率 94.8%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Diethylamine (80 mL, propargyl alcohol (6.4 mL, 0.11 mol), copper(I)iodide (0.7 g), tetrahydrofuran (25 mL), and tetrakis(triphenylphosphine)palladium(o) (1.2 g) were placed in a 250-mL flask under nitrogen. A solution of p-iodoanisole (23.4 g, 0.1 mol) in 40 mL of tetrahydrofuran was added to the reaction dropwise over 30 minutes. The reaction was stirred for 16 hours at room temperature, then evaporated in vacuo to give a dark brown residue. The residue was dissolved in 200 mL of water and extracted four times with diethyl ether (200 mL). The combined extracts were dried over anhydrous sodium sulfate and evaporated to give a dark brown solid that was purified by column chromatography (silica gel), eluting with 9:1 hexane-ethyl acetate to give 15.38 g of the title product.

後処理

  1. customevaporated in vacuo
  2. customto give a dark brown residue
  3. extractionextracted four times with diethyl ether (200 mL)
  4. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  5. customevaporated
  6. customto give a dark brown solid that
  7. customwas purified by column chromatography (silica gel)
  8. washeluting with 9:1 hexane-ethyl acetate

出典と根拠

ORDレコード
ord-effc7818d44b4bbfaa39cb844d6e89c4
出典データセット
uspto-grants-1994_04
特許番号
US05306718

反応ノート

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