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

HRID 1464595노트

반응식

HRID 1464595 반응식
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

참가 물질

8

반응물 3

HCID 7859Propargyl alcoholHCID 8021DiethylamineHCID 696764-Iodoanisole

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-effc7818d44b4bbfaa39cb844d6e89c4
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306718

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