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3. Ex (LiAlH4)

Alkene to Alkane

(LiAlH₄)

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Examples:

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Example 1

LiAlH4 (283 mg, 7.45 mmol) was added to a stirred solution of the SM (1.0 g, 2.98 mmol) in ether (30 mL) at 0 C. The reaction mixture was stirred at 0 C for 1 h. To the mixture was then added H20 (0.280 mL), 3N NaOH (0.280 mL), and H2O (0.840 mL). The resulting precipitate was removed by filtration and the filtrate was concentrated in vacuo to give a yellow oil. The oil (0.9 g) was purified by Prep LC [50 g silica, 0-20% (10% NH3 in MeOH)/(DCM)] to provide to product as a colorless oil. [250 mg]

[Patent Reference: WO2015144799, page 341, (18.8 MB)]

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Example 2

To a mixture of LiAlH4 (78.6 g, 2.00 mol) in dry THF (1 L) at 0 C was added a solution of the SM (78 g, 0.404 mol) in THF (200 mL). The reaction mixture was stirred at 70 C for 16 h. The mixture was cooled to 0 C and quenched slowly with H2O (78 mL), followed by 15% wt aq NaOH (78 mL), then additional H2O (235 mL). After filtration, the filtrate was concentrated in vacuo to provide the product as a light yellow oil. [40 g, 60%]

[Patent Reference: WO2016014463, page 94, (6.7 MB)]