1-Iodopropane → HCID 22261206, compound

HRID 1609920Notes

Reaction equation

HRID 1609920 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([Li])[CH2:23][CH2:24]C.C(I)CC>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:14][C:15]=1[CH2:22][CH2:23][CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 22261167HCID 22261167, compoundHCID 178418339Butyllithium

Product 1

HCID 22261206HCID 22261206, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-(2-Benzyloxyethyl)-2-phenyloxazole (670 mg, 239 mmol) was dissolved in THF (10 mL) and cooled to −78° C. before adding n-butyllithium (1.15 mL of a 2.5 M solution in hexanes). The resulting orange solution was warmed to −65° C., stirred 45 min, and then propyl iodide (1.22 g, 7.17 mmol, 0.70 mL) was added via syringe. The solution was warmed to ambient temperature and stirred 90 min. The mixture was concentrated and the product purified by flash chromatography (100 mL SiO2, hexanes to 20% EtOAc/hexanes) and obtained as a colorless oil (340 mg, 44%): Rf=0.49 in 20% EtOAc/hexanes; 1H NMR (500 MHz, CDCl3) δ 8.00-7.96 (m, 2H), 7.42-7.26 (m, 8H), 4.54 (s, 2H), 3.76 (t, J=7.0 Hz, 2H), 2.83 (t, J=7.0 Hz, 2H), 2.64 (t, J=7.0 Hz, 2H) 1.68 (sextet, J=7.0 Hz, 2H), 0.96 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureThe resulting orange solution was warmed to −65° C.
  2. temperatureThe solution was warmed to ambient temperature
  3. stirringstirred 90 min
  4. concentrationThe mixture was concentrated
  5. customthe product purified by flash chromatography (100 mL SiO2, hexanes to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-94b953b36c3845009bafe061e9c10d89
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

Loading…