Ammonium formate → HCID 22261244, compound

HRID 1609909Notes

Reaction equation

HRID 1609909 reaction equation
C([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:19][CH:20]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[CH:29]([O-])=O.[NH4+]>CO.[Pd]>[CH3:29][C:20]1[O:19][C:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:17][C:16]=1[CH2:15][CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22261150HCID 22261150, compound

Product 1

HCID 22261244HCID 22261244, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[2-(4-Benzyloxyphenoxy)ethyl]-2-phenyloxazole (7.0 g, 18.8 mmol) was dissolved in methanol (150 mL) and treated with palladium on carbon (1.0 g, 10 mol %) and ammonium formate (20.0 g, 0.32 mol). The suspension was heated at reflux for 8 h and then cooled to ambient temperature. The resultant suspension was filtered through Celite with a methanol wash, and the filtrate was concentrated to provide a colorless oil (3.72 g, 70%). 1H NMR (250 MHz, CDCl3) δ 8.84 (s, 1H), 7.81-7.87 (m, 2H), 7.41-7.49 (m, 3H), 6.72 (d, 2H), 6.59 (d, 2H), 4.04 (t, 2H), 2.81 (t, 2H), 2.30 (s, 3H); MS(EI): 282 (M+H), 280 (M−H).

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 8 h
  3. filtrationThe resultant suspension was filtered through Celite with a methanol
  4. washwash
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6d14a06fd3e84d18b7bef886a225d4e4
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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