1-Iodopropane → HCID 22261206, compound

HRID 898429Notes

Reaction equation

HRID 898429 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-316e1f65d37b423988f03f69bc4f2c32
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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