1-Iodonaphthalene → HCID 59779163, compound

HRID 1096728Notes

Reaction equation

HRID 1096728 reaction equation
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.C[O:18][C:19]1[CH2:23][CH2:22][C:21](=O)[CH:20]=1>O1CCCC1>[C:2]1([C:21]2[CH2:22][CH2:23][C:19](=[O:18])[CH:20]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70041-IodonaphthaleneHCID 6434763-Methoxycyclopent-2-en-1-oneHCID 178418339Butyllithium

Product 1

HCID 59779163HCID 59779163, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of 1-iodonapthalene (10.00 g, 39.36 mmol) in tetrahydrofuran (300 mL) at −78° C. was added n-butyllithium (2.5 M in hexanes; 17.49 mL, 43.73 mmol, 1.1 eq.) so that the reaction temperature remained ≦−78° C. The reaction mixture was stirred for 15 minutes. To the reaction mixture was added a solution of 3-methoxy-2-cyclopenten-1-one (5.10 g, 45.48 mmol, 1.16 eq.) in tetrahydrofuran (50 mL) so that the reaction temperature remained ≦−78° C. The reaction mixture was warmed to −20° C. over a 2 h period and the reaction mixture was quenched with a solution of 1N HCl and concentrated in vacuo to remove the organics. A solution of 1N HCl was added and the reaction mixture was stirred for a further 0.5 h and extracted with ethyl acetate (3×100 mL). The organic layers were combined, washed with saturated aqueous sodium bicarbonate (100 mL) followed by brine (100 mL), dried over magnesium sulphate and concentrated in vacuo to afford a yellow oil. The crude oil was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 20%:80%) to afford the desired compound as an off-white solid (4.01 g, 49%). 1H NMR (400 MHz, CDCl3) δ ppm 2.68 (2H, dt, J 2, 4.8 Hz, CH2), 3.16 (2H, td, J 2.4, 4.8 Hz, CH2), 6.51 (1H, t, J 1.6 Hz, CH), 7.54-7.60 (4H, m, ArH), 7.93-8.01 (2H, m, ArH), 8.10-8.18 (1H, m, ArH).

Workup

  1. customremained ≦−78° C
  2. customremained ≦−78° C
  3. customthe reaction mixture was quenched with a solution of 1N HCl
  4. concentrationconcentrated in vacuo
  5. customto remove the organics
  6. additionA solution of 1N HCl was added
  7. stirringthe reaction mixture was stirred for a further 0.5 h
  8. extractionextracted with ethyl acetate (3×100 mL)
  9. washwashed with saturated aqueous sodium bicarbonate (100 mL)
  10. dry with materialdried over magnesium sulphate
  11. concentrationconcentrated in vacuo
  12. customto afford a yellow oil
  13. customThe crude oil was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 20%:80%)

Sources & evidence

ORD record
ord-f16ab44aaddf4ceeab248984edb4ab1f
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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