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12th March 2012 @ 00:01
Reaction complete and consistent with previous attemtps. Used crude in PMY 37-2.

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

Reaction Scheme

Reaction start time: 10.55 12/03/12
PMY 2-5 (400 mg, 1.84 mmol, 1 equiv.) was dissolved in MeOH (30 mL). Sodium borohydride (64 mg, 1.84 mmol, 4 hydride equiv.) was added. After 1 hour TLC shows reaction complete. Acetone (5 mL) added and the reaction stirred at room temperature for 1 hour. The reaction was concentrated under reduced pressure. The residue was stirred with water (15 mL) and extracted with DCM (3 × 10 mL). The combined organic extracts were washed with brine and dried (MgSO4) then concentrated under reduced pressure to a thick orange oil that crystallised on standing (0.41 g). Used without further purification.

TLC (20% EtOAc/hexane) visualised with UV and vanillin:
TLC 1 hour


Risk and Hazard Assessment:
As for Reduction of pyrrole-3-carbaldehyde using sodium borohydride (18-2)
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TLC 1 hour