1,4-Dimethoxy-1-(3-methylbutyl)naphthalen-2(1h)-one → 4-Methoxy-4-(3-methylbutyl)naphthalene-1,3(2h,4h)-dione

HRID 2110578Notes

Reaction equation

HRID 2110578 reaction equation
[CH3:1][O:2][C:3]1([CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13]C)=[CH:5][C:4]1=[O:15]>CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1([CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[CH2:5][C:4]1=[O:15]

Participants

4

Reactant 1

HCID 688388051,4-Dimethoxy-1-(3-methylbutyl)naphthalen-2(1h)-one

Product 1

HCID 688396304-Methoxy-4-(3-methylbutyl)naphthalene-1,3(2h,4h)-dioneYield 90.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of Example 11B (35 mg, 0.127 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 (30 mg, 90%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.30-0.47 (m, 1H), 0.67 (dd, J=13.97, 6.62 Hz, 6H), 0.75-0.93 (m, 1H), 1.10-1.37 (m, 1H), 1.70-1.95 (m, 1H), 1.98-2.21 (m, 1H), 2.81 (s, 3H), 5.70-5.83 (m, 1H), 7.47 (t, 1H), 7.60 (d, 1H), 7.65 (t, 1H), 7.90 (d, J=7.72 Hz, 1H); MS (ESI) m/z 260.9 (M+H)+.

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-cb4dbc4242a74468aabf6d6d33a809c2
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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