Methyl iodide → 1,4-Dimethoxy-1-(3-methylbutyl)naphthalen-2(1h)-one

HRID 2110577Notes

Reaction equation

HRID 2110577 reaction equation
[OH:1][C:2]1([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][C:3]1=[O:14].[H-].[Na+].[CH3:22]I>CN(C)C=O>[CH3:22][O:1][C:2]1([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][C:3]1=[O:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 688403711-Hydroxy-4-methoxy-1-(3-methylbutyl)naphthalen-2(1h)-one

Product 1

HCID 688388051,4-Dimethoxy-1-(3-methylbutyl)naphthalen-2(1h)-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 11A (40 mg, 0.154 mmol) in N,N-dimethylformamide (1 mL) at 0° C. was added 60% wt sodium hydride (24.6 mg, 0.616 mmol). The reaction solution was stirred for 0.5 h and methyliodide (0.038 mL, 0.616 mmol) was added. The solution was stirred 16 h at room temperature, quenched with saturated NH4Cl, and extracted with ethyl acetate. The organic extract was concentrated in vacuo. Column chromatography on silica (20% ethyl acetate/hexane) afforded the title compound as a white solid (35.4 mg, 84%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.55-0.65 (m, 1H), 0.68 (dd, J=6.80 Hz, 6H), 0.85-1.00 (m, 1H), 1.20-1.33 (m, 1H), 1.56-1.96 (m, 2H), 2.76-2.86 (s, 3H), 3.96-4.02 (s, 3H), 5.48-5.84 (s, 1H), 7.25-7.70 (m, 3H), 7.82 (d, J=7.72 Hz, 1H); MS m/z 274.9 (M+H)+.

Workup

  1. stirringThe solution was stirred 16 h at room temperature
  2. customquenched with saturated NH4Cl
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-4498b487d29740f38b2a84fb29627ca3
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

Loading…