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18th September 2012 @ 02:18
Reaction Scheme

AEW 2-1 (1.00 g, 4.60 mmol, 1 equiv.) was dissolved in MeOH (75 mL). Sodium borohydride (174 mg, 4.69 mmol, 4 hydride equiv.) was added. TLC after 2 hours showed some SM still present, after 4 hours still SM so sodium borohydride (44 mg, 1.17 mmol, 1 hydride equiv.) was added. After 30 minutes, reaction complete by TLC. Acetone (25 mL) added to the reaction mixture, stirred for 10 minutes and then concentrated under reduced pressure. Water was added to the redidue and extracted with DCM (3 × 30 mL). The extracts were washed with brine then dried (MgSO4) and concentrated under reduced pressure to an pale brown solid ( mg, mmol, yield. Stored at -20 °C under nitrogen.

Note: The product alcohol is not particularly stable, use very soon after preparation.

1H NMR Data


Risk and Hazard Assessment:
AEW 3-1.pdf


See also:
Reduction of pyrrole-3-carbaldehyde using sodium borohydride (3-1)
Reduction of pyrrole-3-ester PMY 6-1 using lithium aluminium hydride (PMY 15-1)
Reduction of pyrrole-3-carbaldehyde using sodium borohydride (3-1)
Reduction of pyrrole-3-ester PMY 6-1 using lithium aluminium hydride (PMY 15-2)
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