Boron trifluoride etherate → 1-Hydroxy-4-methoxy-1-(3-methylbutyl)naphthalen-2(1h)-one

HRID 2110576Notes

Reaction equation

[OH:1][C:2]1([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[CH2:4][C:3]1=[O:13].B(F)(F)F.[CH3:23]COCC>CO>[OH:1][C:2]1([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:23])=[CH:4][C:3]1=[O:13]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of Example 2D (0.43g, 1.7 mmol) in methanol (2 mL) heated at 60° C. was added boron trifluoride diethyl etherate (0.135 mL, 1.0 mmol). The reaction solution was stirred at 60° C. for 5 h. The solution was quenched with saturated NH4Cl and extracted with ethyl acetate. The organic extract was concentrated in vacuo. Column chromatography on silica (2.5% methanol/dichloromethane) afforded the title compound as a white solid (0.17 g, 37.4%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.70 (dd, J=6.43, 2.39 Hz, 6H), 0.74-0.88 (m, 1H), 0.88-1.06 (m, 1H), 1.16-1.38 (m, 1H), 1.51-1.88 (m, 2H), 3.93 (s, 3H), 5.56 (s, 1H), 5.64 (s, 1H), 7.39 (t, J=7.54 Hz, 1H), 7.52 (t, J=7.54 Hz, 1H), 7.62 (d, 1H), 7.73 (d, J=7.72 Hz, 1H); MS m/z 260.9 (M+H)+.

Workup

customThe solution was quenched with saturated NH4Cl
extractionextracted with ethyl acetate
extractionThe organic extract
concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-e0128c64c7b24c80ab0b51bf584270e7
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517876B2

Reaction notes

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