HCID 22261239, compound → HCID 22261187, compound

HRID 1609963Notes

Reaction equation

HRID 1609963 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]([CH:30]=[CH2:31])[CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH2:30]([C:11]1[CH:10]=[C:9]([OH:8])[CH:29]=[CH:28][C:12]=1[O:13][CH2:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:19][C:20]=1[CH3:21])[CH3:31]

Participants

5

Reactant 2

HCID 22261239HCID 22261239, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22261187HCID 22261187, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-[2-(4-benzyloxy-2-vinylphenoxy)ethyl]-5-methyl-2-phenyloxazole (1.30 g, 3.16 mmol) in ethanol (100 mL) was treated with 5% Pd/C (160 mg) and hydrogen (60 psi) at ambient temperature for 18 h. The mixture was filtered and concentrated in vacuo to give a tan solid (0.65 g, 64%): 1H NMR (400 MHz, CDCl3) δ 7.99 (dd, J=8.3 Hz, 2.0 Hz, 2H), 7.45-7.38 (m, 3H), 6.63 (d, J=2.4 Hz, 1H), 6.50-6.41 (m, 2H), 5.98 (br s, 1H), 4.10 (t, J=6.4 Hz, 2H), 2.95 (t, J=6.4 Hz, 2H), 2.85-2.51 (m, 2H), 2.39 (s, 3H), 1.08 (t, J=7 Hz, 3H); HRMS: Calc'd=324.1599; Found=324.1597.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5edf087e521047f2b052f7d15ff240d3
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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