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1st November 2011 @ 00:18
Product obtained.

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Reduction of pyrrole-3-carbaldehyde, PMY 2-4, to the corresponding alcohol. See PMY 15-* for reduction of the ester to the alcohol.

Reaction Scheme

Reaction start time: 0920 01/11/11
PMY 2-4 (400 mg, 1.84 mmol, 1 equiv.) was dissolved in MeOH (approx 30 mL). Sodium borohydride (70 mg, 1.84 mmol, 4 hydride equiv.) was added. After 100 minutes, TLC, shows reaction almost complete. After a further 20 minutes, acetone (approx 5 mL) was added. Stirred for 5 minutes, then concentrated under reduced pressure. Water was added to the redidue and extracted with DCM (3 × 15 mL). The extracts were washed with brine then dried (MgSO4) and concentrated under reduced pressure to a white solid (424 mg, 105%). Stored at -20 °C under nitrogen.

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

TLC (25% EtOAc/hexane) visualised with UV and vanillin:
TLC 100 mins

Left and right are both 100 minutes. Left plate spotted and eluted after 5 minutes. Right plate spotted and eluted immediately.

Risk and Hazard Assessment:
As for 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.

See also:
Reduction of pyrrole-3-ester PMY 6-1 using lithium aluminium hydride (PMY 15-2)
Reduction of pyrrole-3-ester PMY 6-1 using lithium aluminium hydride (PMY 15-1)
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Reaction Scheme
TLC 100 mins