HCID 22261108, compound → HCID 22261226, compound

HRID 898457Notes

Reaction equation

HRID 898457 reaction equation
C([O:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[C:11]([CH2:30][CH2:31][CH3:32])[CH:10]=1)C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[CH3:21][C:20]1[O:19][C:18]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:17][C:16]=1[CH2:15][CH2:14][O:13][C:12]1[CH:28]=[CH:29][C:9]([OH:8])=[CH:10][C:11]=1[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 2

HCID 22261108HCID 22261108, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22261226HCID 22261226, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[2-(4-benzyloxy-2-propylphenoxy)ethyl]-5-methyl-2-phenyloxazole. (1.2 g, 2.8 mmol) in THF (50 mL) was treated with 5% Pd/C (0.15 g) and hydrogen (60 psi) at ambient temperature for 18 h. The mixture was filtered and concentrated. The crude product was purified by radial chromatography using 15% ethyl acetate in hexanes to give a tan solid (0.74 g, 78%): 1H. NMR (400 MHz, CDCl3) δ 7.99 (dd, J=7.8 Hz, 2.4 Hz, 2H), 7.44-7.39 (m, 3H), 6.65-6.47 (m, 3H), 4.11 (t, J=6.4 Hz, 2H), 2.95 (t, J=6.4 Hz, 2H), 2.43 (t, J=7.8 Hz, 2H), 2.39 (s, 3H), 1.46 (q, J=7.2 Hz, 2H), 0.85 (t, J=7 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe crude product was purified by radial chromatography

Sources & evidence

ORD record
ord-c4a670511e844fbab547e76cec0dfc8c
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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