1-(Benzyloxy)-4-methoxy-1-(3-methylbutyl)naphthalen-2(1h)-one → 4-(Benzyloxy)-4-(3-methylbutyl)naphthalene-1,3(2h,4h)-dione

HRID 2110580Notes

Reaction equation

HRID 2110580 reaction equation
[CH2:1]([O:8][C:9]1([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([O:19]C)=[CH:11][C:10]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[OH-].[Na+]>[CH2:1]([O:8][C:9]1([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[CH2:11][C:10]1=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 688418191-(Benzyloxy)-4-methoxy-1-(3-methylbutyl)naphthalen-2(1h)-one

Product 1

HCID 688408004-(Benzyloxy)-4-(3-methylbutyl)naphthalene-1,3(2h,4h)-dioneYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of Example 12A (26 mg, 0.074 mmol) in methanol (0.25 mL) and 1 N NaOH (0.25 mL) was stirred at 40° C. for 6 hours. The solution was concentrated in vacuo. Column chromatography on silica (7% methanol/dichloromethane) afforded the title compound (23 mg, 91%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.29-0.46 (m, 1H), 0.69 (dd, J=13.97, 6.62 Hz, 6H), 0.80-0.95 (m, 1H), 1.25-1.41 (m, 1H), 1.97 (m, 1H), 2.27 (m, 1H), 3.83 (d, J=10.66 Hz, 1H), 4.04-4.20 (m, 1H), 5.89 (s, 1H), 7.18-7.42 (m, 5H), 7.44-7.59 (m, 1H), 7.71 (br. s, 2H) 7.94 (br. s, 1H), 11.76 (s, 1H); MS (ESI) m/z 337.1 (M+H)+.

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-05e2ba860de3492a92c454eaf04c3be0
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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