63
Q. Zhang et al.
Paper
Synthesis
1,2,3-Trimethoxy-5-(methoxymethyl)benzene (31)39
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NaAuCl4·2 H2O (39.8 mg, 0.1 mmol, 0.05 equiv) was added to a solu-
tion of silyl ether 30 (624 mg, 2 mmol) in MeOH (4 mL), and the mix-
ture was refluxed for 24 h. The mixture was then cooled to r.t., diluted
with EtOAc (10 mL), filtered through activated alumina, and concen-
trated in vacuo. The residue was purified by flash column chromatog-
raphy [silica gel, EtOAc–PE (1:10)] to give a colorless oil; yield: 266 mg
(63%).
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1H NMR (300 MHz, CDCl3): δ = 6.57 (s, 2 H), 4.39 (s, 2 H), 3.87 (s, 6 H),
3.84 (s, 3 H), 3.41 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 153.26, 137.46, 133.85, 104.61, 74.85,
60.76, 58.11, 56.05.
MS (ESI, MeOH): m/z = 235 [M + Na]+.
HRMS-ESI: m/z [M + Na]+ calcd for C11H16NaO4: 235.0946; found:
235.0948.
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Acknowledgment
This work was supported by the National Natural Science Foundation
of China (21302119), the Research Fund for the Doctoral Program of
Higher Education of China (20100202120002), and the Fundamental
Research Funds for the Central Universities (GK201302017).
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