Iodide Ion → 5-(4-Methoxyphenyl)pent-4-yn-1-ol

HRID 25100

Reaction equation

HRID 25100 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[I-].[CH2:11]([OH:16])[CH2:12][CH2:13][C:14]#[CH:15]>C(NCC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]#[C:14][CH2:13][CH2:12][CH2:11][OH:16])=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 30165Iodide IonHCID 696764-IodoanisoleHCID 793464-Pentyn-1-ol

Product 1

HCID 115501385-(4-Methoxyphenyl)pent-4-yn-1-olYield 88.9%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 24290Palladium ChlorideCatalystHCID 8021DiethylamineSolvent

Procedure

4-Iodoanisol (10 g, 42 mmol), palladium (II) chloride (0.2 g, 1.1 mmol) and triphenylphosphine (0.6 g, 2.2 mmol) were dissolved in diethylamine (100 mL) then cupper(I) iodide (0.5 g, 2.2 mmol) and 4-pentyn-1-ol (5 mL, 53 mmol) were added. The reaction mixture was stirred overnight at room temperature, then the solvent was removed under reduced pressure. Ethyl acetate (150 mL) was added to the residue and the mixture was washed with 2N HCl, brine and water. The organic fraction was isolated, dried with sodium sulfate and the solvent was removed under reduced pressure. The product 16 (7.1 g. 87%) was isolated by flash chromatography (silica gel, 1:2 ethyl acetate/hexanes) as an oily yellow solid. 1H NMR (300 MHz, CDCl3) δ1.88 (m, 2H), 2.53 (m, 2H), 3.72 (s, 3H), 3.74 (m, 2H), 6.83 (d, 2H), 7.45 (d, 2H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionEthyl acetate (150 mL) was added to the residue
  3. washthe mixture was washed with 2N HCl, brine and water
  4. customThe organic fraction was isolated
  5. dry with materialdried with sodium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-25ced7eb4bce4b60b9dcf3c7dc51c11f
Source dataset
uspto-grants-2005_02
Patent number
US06858614B2

Linked notes

Loading…