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22nd February 2012 @ 22:37
Used crude in PMY 37-1

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Reduction of pyrrole-3-carbaldehyde, PMY 2-5, to the corresponding alcohol.

Reaction Scheme

Reaction start time: 10.30 23/02/12
PMY 2-5 (200 mg, 0.92 mmol, 1 equiv.) was dissolved in MeOH (approx 15 mL). Sodium borohydride (32 mg, 0.92 mmol, 4 hydride equiv.) was added. After 3 hours, reaction not complete. The batch of borohydride seemed wet, potentially partially hydrolysed. Further sodium borohydride (32 mg, 0.92, 4 hydride equiv.) added. After a further hour, the reaction is essentially complete by TLC. Acetone (5 mL) added to the reaction. After stirring for 10 minutes, the reaction was concentrated under reduced pressure. The residue was dissolved in water (10 mL) and DCM (10 mL). The layers were separated and the aqueous layer extracted with DCM (2 × 10 mL). The combined organic extracts were washed with brine, then dried (MgSO4) and concentrated under reduced pressure to a thick orange oil. Used directly in: Synthesis of ether-linked analogue of TCMDC-123812 (PMY 37-1)

TLC (25% EtOAc/hexane) visualised with UV and vanillin:
TLC 3 hours


Risk and Hazard Assessment:
As for Reduction of pyrrole-3-carbaldehyde using sodium borohydride (PMY 18-1) and Reduction of pyrrole-3-ester PMY 6-1 using lithium aluminium hydride (PMY 15-2), except using the less hazardous sodium borohydride as the reductant.
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TLC 3 hours