Potassium Carbonate → HCID 72546825, compound

HRID 2280088Notes

Reaction equation

HRID 2280088 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]1[CH2:13][CH2:14][C:15](=[O:16])[C:7]1=[C:6]2[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1.[C:26](=O)([O-])[O-].[K+].[K+].C/C(/[O-])=C(/P(OC)(OC)=O)\[N+]#N>CO>[CH3:1][N:2]([CH3:25])[C:3]1[CH:4]=[C:5]2[C:10]([CH:9]=[C:8]3[CH2:13][CH2:14][C:15](=[O:16])[C:7]3=[C:6]2[C:17]2[CH:18]=[CH:19][C:20]([C:21]#[CH:26])=[CH:23][CH:24]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 72546824HCID 72546824, compoundHCID 178502985HCID 178502985, compound

Product 1

HCID 72546825HCID 72546825, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A flame-dried 25 mL two-necked round-bottomed flask equipped with a nitrogen inlet, a septum and a stir bar was charged with compound 19 (0.031 g, 0.094 mmol) and methanol (7 mL). To this solution was added potassium carbonate (0.064 g, 0.48 mmol) followed by the Bestmann-Ohira reagent (0.054 g, 0.28 mmol) in methanol (5 mL). The reaction was stirred at rt overnight. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 2:8). The solution was diluted with ether (10 mL) and then transferred to a separatory funnel containing sat'd aq NaHCO3 solution (15 mL). The layers were separated and the organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel flash column chromatography, eluting with AcOEt/n-hexane 2:8, to provide 0.018 g of the title compound as an orange solid in a 59% yield.

Workup

  1. customA flame-dried 25 mL two-necked round-bottomed flask equipped with a nitrogen inlet
  2. customThe consumption of the starting material
  3. additionThe solution was diluted with ether (10 mL)
  4. customtransferred to a separatory funnel
  5. additioncontaining sat'd aq NaHCO3 solution (15 mL)
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by silica gel flash column chromatography
  11. washeluting with AcOEt/n-hexane 2:8

Sources & evidence

ORD record
ord-c27a68a5884b4ed1a4228de4531aac11
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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