2-Methyl-3-butyn-2-ol → HCID 11042846, compound

HRID 1359238Notes

Reaction equation

HRID 1359238 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](Br)[CH:7]=[CH:6]2.[CH3:14][C:15]([OH:19])([C:17]#[CH:18])[CH3:16]>C(NCC)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>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:18]#[C:17][C:15]([CH3:16])([OH:19])[CH3:14])[CH:7]=[CH:6]2

Participants

6

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 787862-Bromo-6-methoxynaphthalene

Product 1

HCID 11042846HCID 11042846, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

A mixture of 6-methoxy-2-bromonaphthalene (14.23 g, 60.0 mmol), copper (I) iodide (0.17 g, 0.90 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.63 g, 0.90 mmol), and 2-methyl-3-butyn-2-ol (8.7 mL, 90 mmol) in diethylamine (100 mL) was heated at reflux for 16 hours, cooled to room temperature and solvent evaporated. The residue was purified by flash chromatography using 15-25% ethyl acetate in hexane as an eluant. Drying at 80° C. for 20 minutes afforded 4-(6-methoxy-2-naphthyl)-2-methyl-3-butyn-2-ol as a light orange solid (14.4 g), mp: 118-119° C. 1HNMR (300 MHz, DMSO-d6): δ7.95 (s, 1H), 7.75-7.85 (m, 2H), 7.4 (dd, 1H, J=8.4 Hz and 1.5 Hz), 7.35 (d, 1H, J=2.4 Hz), 7.2 (dd, 1H, J=8.5 Hz and 1.5 Hz), 5.5 (s, 1H), 3.9 (s, 3H), and 1.5 ppm (s, 6H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customsolvent evaporated
  4. customThe residue was purified by flash chromatography
  5. customDrying at 80° C. for 20 minutes

Sources & evidence

ORD record
ord-38eff65cc5d1450d8ec7066a293884b0
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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