Hydrochloric Acid → HCID 57817098, compound

HRID 886649Notes

Reaction equation

HRID 886649 reaction equation
P([O:9][CH:10]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][Si](C(C)(C)C)(C)C)[CH:20]=1)[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(OCC)(OCC)=O.[OH-:33].[K+].Cl.C1(=O)[O:40][CH2:39][CH2:38]O1.N1[CH:47]=[CH:46]C=CC=1>C1COCC1>[OH:33][CH2:46][CH2:47][O:9][CH:10]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:38][CH2:39][OH:40])[CH:20]=1)[C:11]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:18]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 1049PyridineHCID 7303Ethylene carbonateHCID 14797Potassium HydroxideHCID 68969881HCID 68969881, compound

Product 1

HCID 57817098HCID 57817098, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of Compound 8 (0.25 mmol) in 10 mL of THF was added 0.55 mmol of KOH. The solution was heated to reflux and was stirred for 15 mm, poured into 10 mL of 1 N HCl and extracted with methylene chloride (4×50 mL). The organic phase was washed with brine, dried with Mg2SO4, filtered through a plug of activated charcoal and silica gel, and evaporated under reduced pressure. The resulting oil was dissolved in 15 mL of dry THF under a dry nitrogen atmosphere and ethylene carbonate dissolved in dry THF (80 mg, 1 mmol) was added and the solution cooled to 0° C. To this solution with rapid stirring was added dry pyridine (0.5 mmol). The solution was stirred for, 1 hour and then poured into 10 mL of 1 N HCl and extracted with methylene chloride (4×50 mL). The organic phase was washed with brine, dried with Mg2SO4, filtered through a plug of activated charcoal and silica gel, and evaporated under reduced pressure. Overall yield: ˜0.08 mmol (35%). 1H NMR (CDCl3, TMS) δ, 7.629 (m, J 7.55 Hz, 2H), 7.41-7.27 (m, 3H), 7.18 (t, 1H), 6.91 (s, 1H) 6.87 (m, 1H), 6.77 (m, 1H), 6.07 (s, 1H), 4.15-4.05 (m, 2H), 4.03-3.96 (m, 4H), 3.84 (m, 2H), 2.28 (d, 1H), 2.08 (d, 1H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. extractionextracted with methylene chloride (4×50 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried with Mg2SO4
  6. filtrationfiltered through a plug of activated charcoal and silica gel
  7. customevaporated under reduced pressure
  8. dissolutionThe resulting oil was dissolved in 15 mL of dry THF under a dry nitrogen atmosphere
  9. additionwas added
  10. stirringTo this solution with rapid stirring
  11. stirringThe solution was stirred for, 1 hour
  12. extractionextracted with methylene chloride (4×50 mL)
  13. washThe organic phase was washed with brine
  14. dry with materialdried with Mg2SO4
  15. filtrationfiltered through a plug of activated charcoal and silica gel
  16. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2e18764534d3489b88138e08aaada677
Source dataset
uspto-grants-2012_08
Patent number
US08246869B2

Reaction notes

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