yogi
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possible to use NaBH4 for 3,4,5-Trimethoxyphenylacetonitrile -> Mescaline?
instead of LiAlH4? any thoughts?
[Edited on 29-12-2004 by yogi]
[Edited on 29-12-2004 by yogi]
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enima
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yes it can,
yes, it can be used to reduce that triple bond but expect lower yields than the LiAH method.
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NaBH4 (4.56g, 120 mmol) was added to a solution of Me3SiCl (26.04 g, 240 mmol) in THF (100 mL) and the mixture refluxed for 3 h under argon. A
solution of 3,4-dimethoxybenzylcyanide (10 g, 56.4 mmol) in THF (50 mL) was then added over the course of 10 min. The solution was refluxed for a
further 10 h. After cooling, 100 mL MeOH were cautiously added and the volatiles removed in vacuo. The residue was taken up in dilute HC1 and washed
with ether. The aqueous solution was treated with excess dilute NaOH and then repeatedly extracted with CH2Cl2. The organic extracts were combined,
dried over Na2SO4, and the solvent evaporated to afford 2-(3,4-dimethoxyphenyl)ethylamine (pure by 1H NMR). Yield after kugelrohr distillation 9.16 g
(90%).
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yogi
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ok well, yield is a major factor for this compound. Good info!
but if weighing the pros and cons of NaBH4 vs. LiAlH4 i tend to think NaBH4 is better to use...
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