Toluene → HCID 18705852, compound

HRID 2287834Notes

Reaction equation

HRID 2287834 reaction equation
C([N:3]([CH2:6]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[C:25]([OH:29])([CH3:28])([CH3:27])[CH3:26].[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:25]([O:29][C:6]([NH:3][CH:32]([CH2:33][C:34]#[CH:35])[CH2:31][C:30]#[CH:36])=[O:15])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 18705852HCID 18705852, compound

Procedure

Triethylamine (19.5 g, 0.193 mol) was added to a solution of 2-(propyn-2-yl)-4-pentynoic acid (34, 25.0 g, 0.184 mol; J. Chem. Soc., Perkin Trans. I, 1215-1224 (1986)) in toluene (200 ml) with cooling. Diphenylphosphoryl azide (50.3 g, 0.184 mol) was added, and the mixture was stirred at room temperature for 15 minutes and heated on the steam bath until the evolution of gas ceased. Dry t-butanol (150 ml) was added, and the mixture was heated on the steam bath for 24 hours. The solvent was removed under vacuum, and the mixture was diluted with water and extracted twice with diethylether. The combined extracts were washed twice with 10% sodium carbonate solution and once with brine. The solution was dried (MgSO4), and the solvent was removed under vacuum to leave a solid. Purification by flash chromatography on silica gel eluting with ethyl acetate/hexane gave a white solid which was crystallized from hexane to give 4-(t-butyloxycarbonylamino)heptan-1,6-diyne as colorless crystals (m.p. 64-67° C.).

Workup

  1. temperaturewith cooling
  2. temperatureheated on the steam bath until the evolution of gas
  3. temperaturethe mixture was heated on the steam bath for 24 hours
  4. customThe solvent was removed under vacuum
  5. additionthe mixture was diluted with water
  6. extractionextracted twice with diethylether
  7. washThe combined extracts were washed twice with 10% sodium carbonate solution and once with brine
  8. dry with materialThe solution was dried (MgSO4)
  9. customthe solvent was removed under vacuum
  10. customto leave a solid
  11. customPurification by flash chromatography on silica gel eluting with ethyl acetate/hexane
  12. customgave a white solid which
  13. customwas crystallized from hexane

Sources & evidence

ORD record
ord-ba27a9425bb246ab8f11d639143cef80
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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