Sodium Borohydride

Used Chemicals

• Sodium Borohydride [S0480]
• 4',5'-Dimethoxy-2'-nitroacetophenone [D5477]
• THF
• Methanol

Procedure

Sodium borohydride (250 mg, 6.70 mmol) was separately added to a solution of 4',5'-dimethoxy-2'-nitroacetophenone (1.50 g, 6.70 mmol) in THF (12 mL) and methanol (3 mL) at 0 °C. Then the mixture was allowed to warm to room temperature and stirred for 1.5 hours. The solution was diluted with dichloromethane (15 mL) and washed with water (15 mL x 3) and brine (15 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure. The residue was diluted with THF (6 mL) and the mixture was stirred at 37 °C. Hexane (10 mL) was added to the solution and the mixture was stirred at 0 °C and filtered to give 1 (1.16 g、77%) as a yellow solid.

Experimenter’s Comments

The reaction mixture was monitored by TLC (hexane:ethyl acetate = 1:1, Rf = 0.47) and UPLC.
To avoid moisture absorption of sodium borohydride, weighing was done quickly.

Analytical Data

Compound 1

¹H NMR (400 MHz, CDCl₃); δ 7.57 (s, 1H), 7.31 (s, 1H), 5.58 (q, J = 5.4 Hz, 1H), 4.01 (s, 3H), 3.95 (s, 3H), 1.56 (d, J = 5.4 Hz, 3H).

Lead Reference

• Triggering a [2]Rotaxane Molecular Shuttle by a Photochemical Bond-Cleavage Strategy
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References

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References

• J. M. Khurana, D. Magoo, Synth. Commun. 2010, 40, 2908.