Nitrogen → HCID 13426869, compound

HRID 978236Notes

Reaction equation

HRID 978236 reaction equation
N#N.[OH-].[K+].[CH3:5][O:6][C:7]12[CH2:14][CH2:13][CH:10]([CH:11]=[CH:12]1)[CH2:9][CH:8]2[C:15]([O:17]C)=[O:16]>CO.O>[CH3:5][O:6][C:7]12[CH2:14][CH2:13][CH:10]([CH:11]=[CH:12]1)[CH2:9][CH:8]2[C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 947NitrogenHCID 14797Potassium HydroxideHCID 27241515259-50-7

Product 1

HCID 13426869HCID 13426869, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

In a 3 liter flask equipped with a mechanical stirrer, thermometer, reflux condenser, addition funnel and N2 atmosphere, potassium hydroxide (4.59 mole) was dissolved in methanol (1 L). To the resulting hot solution was added, over a five minute period, methyl 1-methoxybicyclo[2.2.2]oct-5-ene-2-carboxylate (1.53 mole) and the resulting light brown solution was heated to reflux for 5 hours. The reaction was then diluted with H2O (700 ml) and stripped under reduced pressure to a tan slimy solid. This solid was dissolved in fresh H2O (1 L) and washed with methylene chloride (1×500 ml). The separated aqueous layer was acidified to pH 1.5 with 420 ml conc. HCl at reduced temperature and extraced with methylene chloride (3×500 ml). The combined organic layers were washed with H2O (1 L) and brine. Drying and stripping under reduced pressure yielded 87.8% of title product as brown solids; mp 77°-81°; pnmr/CDCl3 /TMS/delta 1.65-2.0 (m, 6, C3H, C7H, C8H), 2.6-2.8 (m, 2, C4H, C2H), 3.4 (s, 3, OCH3), 6.2 (m, 2, C5H, C6H).

Workup

  1. customIn a 3 liter flask equipped with a mechanical stirrer
  2. temperaturethermometer, reflux
  3. additioncondenser, addition funnel
  4. additionTo the resulting hot solution was added, over a five minute period
  5. temperatureto reflux for 5 hours
  6. washwashed with methylene chloride (1×500 ml)
  7. washThe combined organic layers were washed with H2O (1 L) and brine
  8. customDrying

Sources & evidence

ORD record
ord-46215961f4114387801decb2de83822c
Source dataset
uspto-grants-1987_05
Patent number
US04663474

Reaction notes

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