Propargyl alcohol → (E)-6,6-dimethyl-4-hepten-2-yn-1-ol

HRID 1464782Notes

Reaction equation

HRID 1464782 reaction equation
I/[CH:2]=[CH:3]/[C:4]([CH3:7])([CH3:6])[CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N)CCC.[CH2:32]([OH:35])[C:33]#[CH:34]>O1CCCC1.[Cu]I.[Pd](Cl)Cl.C(OCC)(=O)C.O>[CH3:5][C:4]([CH3:7])([CH3:6])/[CH:3]=[CH:2]/[C:34]#[C:33][CH2:32][OH:35]

Participants

10

Reactant 4

HCID 7859Propargyl alcoholHCID 8007ButylamineHCID 11776TriphenylphosphineHCID 11063689(E)-1-iodo-3,3-dimethylbut-1-ene

Product 1

HCID 19917005(E)-6,6-dimethyl-4-hepten-2-yn-1-ol

Reagents, catalysts & solvents 5

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.63 g of (E)-1- iodo-3,3-dimethyl-1-butene [see J. Org. Chem., 43, 4424 (1978)] was dissolved in 10 ml of tetrahydrofuran, and 31 mg of triphenylphosphine, 29 mg of copper(I) iodide, 11 mg of palladium chloride, 1.5 ml of n-butylamine and 0.35 ml of propargyl alcohol were added. The mixture was stirred overnight at room temperature, and then water and ethyl acetate were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1] to give 0.27 g of the captioned compound as a pale brown oil.

Workup

  1. customThe organic layer separated
  2. customthe product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1]

Sources & evidence

ORD record
ord-8bfc60aedb7d4839b58de804983eda20
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

Loading…