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

HRID 1464595Notes

Reaction equation

HRID 1464595 reaction equation
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

Participants

8

Reactant 3

HCID 7859Propargyl alcoholHCID 8021DiethylamineHCID 696764-Iodoanisole

Product 1

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

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-effc7818d44b4bbfaa39cb844d6e89c4
Source dataset
uspto-grants-1994_04
Patent number
US05306718

Reaction notes

Loading…