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12th March 2012 @ 02:46
Traces of products obtained.

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Synthesis of the ether-linked analogue of TCMDC-123812 from alcohol PMY 18-3 and 2-bromoacetamide.

37-1.png

Reaction Start Time: 15.00 12/03/12
Sodium hydride (60% in mineral oil, 72 mg, 1.82 mmol, 2.0 equiv.) was suspended in THF (5 mL) in an ice bath. PMY 18-3 (crude, 0.20 g, 0.91 mmol, 1 equiv.) was dissolved in THF (4 mL) and added portionwise to the sodium hydride suspension and the reaction allowed to warm to room temperature. After 15 minutes, 2-bromoacetamide (252 mg, 1.82 mmol, 2.0 equiv.) as a partial solution in THF (5 mL) was added dropwise to the pale yellow solution. A white precipitate forms on addition. After 1 hour at room temperature, TLC shows no reaction. Reaction heated to 60 °C. After 17 hours, TLC shows only traces of products, consistent with PMY 37-3.

TLC (50% EtOAc/hexane) visualised with UV and vanillin:
TLC 17 hours
TLC 1 hour


See also:
Reduction of pyrrole-3-carbaldehyde using sodium borohydride (18-3)
Synthesis of ether-linked analogue of TCMDC-123812 (PMY 37-3)
Synthesis of ether-linked analogues of TCMDC-123812 and TCMDC-123794 (PMY 19-1)
Synthesis of ether-linked analogue of TCMDC-123794 (PMY 17-2)
Synthesis of ether-linked analogue of TCMDC-123794 (PMY 17-1)

Risk and Hazard Assessment:
As for: Synthesis of ether-linked analogue of TCMDC-123812 (PMY 37-1)
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TLC 1 hour
TLC 17 hours