Ammonia → HCID 19029811, compound

HRID 2256376Notes

Reaction equation

HRID 2256376 reaction equation
N.[Li].[CH3:3][O:4][C:5]1[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([O:22][CH3:23])=[C:15]2[C:6]=1[C:7]1([CH3:26])[C:12]([CH2:13][CH2:14]2)=[C:11]([CH3:24])[C:10](=[O:25])[CH2:9][CH2:8]1>C1COCC1>[CH3:3][O:4][C:5]1[CH:18]=[C:17]([CH:19]([CH3:20])[CH3:21])[C:16]([O:22][CH3:23])=[C:15]2[C:6]=1[C:7]1([CH3:26])[CH:12]([CH2:13][CH2:14]2)[CH:11]([CH3:24])[C:10](=[O:25])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 3028194LithiumHCID 11099521HCID 11099521, compound

Product 1

HCID 19029811HCID 19029811, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 15.6 ml of liquid ammonia was added 28.5 mg of lithium metal at -78° C. and the mixture was stirred for 5 minutes. Then, 15.6 ml of a THF solution containing 500 mg of the compound obtained in Example 1 was slowly added dropwise. After the mixture was stirred at -78° C. for 1.5 hours, the ammonia was distilled off and the residue was diluted with water and extracted with diethyl ether. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting crude product was purified by silica gel column chromatography (eluent=diethyl ether:n-hexane:chloroform=5:50:1) to provide 270 mg of the object compound.

Workup

  1. additionwas slowly added dropwise
  2. stirringAfter the mixture was stirred at -78° C. for 1.5 hours
  3. distillationthe ammonia was distilled off
  4. additionthe residue was diluted with water
  5. extractionextracted with diethyl ether
  6. washThe organic layer was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe resulting crude product was purified by silica gel column chromatography (eluent=diethyl ether:n-hexane:chloroform=5:50:1)

Sources & evidence

ORD record
ord-149e219c1c0a44218a097b50dc06d18c
Source dataset
uspto-grants-1997_08
Patent number
US05654343

Reaction notes

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