Propargyl alcohol → HCID 18467037, compound

HRID 2229248Notes

Reaction equation

HRID 2229248 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[CH2:12]([OH:15])[C:13]#[CH:14]>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:14]#[C:13][CH2:12][OH:15]

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 113722-Bromonaphthalene

Product 1

HCID 18467037HCID 18467037, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-bromonaphthalene (19.83 g), CuI (1.59 g), 2-propyn-1-ol (10 ml) and dichlorobis(triphenylphosphine)palladium (II) (2.00 g) in triethylamine (300 ml) was stirred under argon atmosphere at 50° C. for 72 hours. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was extracted with ethyl acetate and the extract was washed with water and brine, dried over Na2SO4and concentrated in vacuo. The residue was chromatographed on silica gel (hexane:ethyl acetate=5:2) followed by recrystallization from hexane-ethyl acetate to give the titled compound (14.92 g) as a colorless powder.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. extractionThe residue was extracted with ethyl acetate
  4. washthe extract was washed with water and brine
  5. customdried over Na2SO4and
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel (hexane:ethyl acetate=5:2)
  8. customfollowed by recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-8731743aad71419cb16045fe65698279
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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