Benzyl Bromide → 1-(Benzyloxy)-4-methoxy-1-(3-methylbutyl)naphthalen-2(1h)-one

HRID 2110579Notes

Reaction equation

HRID 2110579 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+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([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])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 688403711-Hydroxy-4-methoxy-1-(3-methylbutyl)naphthalen-2(1h)-one

Product 1

HCID 688418191-(Benzyloxy)-4-methoxy-1-(3-methylbutyl)naphthalen-2(1h)-oneYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 11A (25 mg, 0.094 mmol) in N,N-dimethylformamide (1 mL) at 0° C. was added 60% wt sodium hydride (15.4 mg, 0.384 mmol). The reaction solution was stirred for 0.5 h and benzylbromide (0.046 mL, 0.384 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 an oil (29 mg, 86%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.71 (dd, 6H), 0.80-1.03 (m, 2H), 1.19-1.38 (m, 1H), 1.69-2.04 (m, 2H), 3.85 (d, J=10.66 Hz, 1H), 3.98 (s, 3H), 4.04 (d, J=11.03 Hz, 1H), 5.84 (s, 1H) 7.19-7.39 (m, 5H), 7.40-7.57 (m, 1H), 7.58-7.71 (m, 2H), 7.85 (d, J=7.72 Hz, 1H); MS m/z 351.1 (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-1dff1ea069fc4411bac1ce1cbc347038
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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