HCID 22261206, compound → HCID 22261134, compound

HRID 898430Notes

Reaction equation

HRID 898430 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:14][C:15]=1[CH2:16][CH2:17][CH3:18])C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[C:19]1([C:13]2[O:14][C:15]([CH2:16][CH2:17][CH3:18])=[C:11]([CH2:10][CH2:9][OH:8])[N:12]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 22261206HCID 22261206, compound

Product 1

HCID 22261134HCID 22261134, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(2-Benzyloxyethyl)-2-phenyl-5-propyloxazole (340 mg, 1.05 mmol) was dissolved in THF (5 mL) and treated with Pearlman's catalyst (170 mg). The solution was stirred vigorously under a hydrogen atmosphere (1 atm) for 90 min, and then the mixture was filtered through celite. The celite was rinsed with CH2Cl2 and the solution dried (MgSO4), filtered and concentrated to a clear, colorless oil: Rf=0.25 in 60% EtOAc/hexanes; 1H NMR (300 MHz, CDCl3) δ 8.00-7.96 (m, 2H), 7.44-7.22 (m, 2H), 3.92 (br s, 2H), 2.73 (t, J=5.5 Hz, 2H), 2.65 (t, J=7.0 Hz, 2H) 1.70 (sextet, J=7.0 Hz, 2H), 0.98 (t, J=7.0 Hz, 3H).

Workup

  1. filtrationthe mixture was filtered through celite
  2. washThe celite was rinsed with CH2Cl2
  3. dry with materialthe solution dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a clear, colorless oil

Sources & evidence

ORD record
ord-aeac70ea59df428fb993b32f2cabe6ce
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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