tert-Butanol → HCID 18705852, compound

HRID 1585167Notes

Reaction equation

HRID 1585167 reaction equation
[CH2:1]([CH:4]([CH2:8][C:9]#[CH:10])C(O)=O)[C:2]#[CH:3].C([N:13]([CH2:16]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.[C:35]([OH:39])([CH3:38])([CH3:37])[CH3:36]>C1(C)C=CC=CC=1>[C:35]([O:39][C:16]([NH:13][CH:4]([CH2:1][C:2]#[CH:3])[CH2:8][C:9]#[CH:10])=[O:25])([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 136736532-(prop-2-yn-1-yl)pent-4-ynoic acid

Product 1

HCID 18705852HCID 18705852, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(2-propynyl)-4-pentynoic acid 42 (25.0 g, 0.184 mol) in toluene (200 ml) was added triethylamine (19.5 g, 0.193 mol) with cooling. Diphenylphosphoryl azide (50.5 g, 0.184 mol) was added, and the mixture was stirred at room temperature for 15 minutes. The mixture was heated on the steam bath until the reaction became exothermic. When the reaction subsided, the heating was continued for an additional 10 minutes during which time the evolution of gas ceased. Dry t-butanol (150 ml) was added, and the mixture was heated at reflux on the steam bath for 24 hours. The solvent was removed under vacuum, and the residue was diltued with water and extracted twice with diethylether. The combined aqueous extracts were washed with water (2×), 10% sodium carbonate solution, and brine. The solution was dried (MgSO4), and the solvent was removed under vacuum to leave crude 43 as a red-brown solid (35.35 g). A sample (3.2 g) was purified via flash chromatography (230-400 mesh silica gel, 10% ethyl acetate in hexane) to give a colorless solid (2.69 g). Crystallization from hexane gave the title compound (43) as colorless crystals (m.p. 64-67° C.).

Workup

  1. temperaturewith cooling
  2. temperatureThe mixture was heated on the steam bath until the reaction
  3. waitthe heating was continued for an additional 10 minutes during which time
  4. temperaturethe mixture was heated
  5. temperatureat reflux on the steam bath for 24 hours
  6. customThe solvent was removed under vacuum
  7. extractionextracted twice with diethylether
  8. washThe combined aqueous extracts were washed with water (2×), 10% sodium carbonate solution, and brine
  9. dry with materialThe solution was dried (MgSO4)
  10. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d17ff667186d4b1da8a02005ff0fe65e
Source dataset
uspto-grants-1999_08
Patent number
US05936000

Reaction notes

Loading…