Methanol → HCID 58496327, compound

HRID 2039663Notes

Reaction equation

HRID 2039663 reaction equation
CO.[F:3][CH:4]([F:32])[O:5][C:6]1[C:11]2[O:12][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=3[C:10]=2[C:9]([C:22]2[O:23][CH:24]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:26]=2)=[CH:8][CH:7]=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][C:11]3[C:6]([O:5][CH:4]([F:3])[F:32])=[CH:7][CH:8]=[C:9]([C:22]4[O:23][CH:24]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:26]=4)[C:10]=3[C:14]=2[CH:15]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 46846425HCID 46846425, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58496327HCID 58496327, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methanol (100 mL) and ethyl acetate (100 mL) was added to the ethyl 2-(4-(difluoromethoxy)-8-nitrodibenzo[b,d]furan-1-yl)1,3-oxazole-4-carboxylate (0.8 g, 1.91 mmol) from step 7 of example 47. To the reaction mixture, palladium-carbon (0.30 g) was added. The reaction mixture was transferred to the hydrogenation flask and hydrogenation was performed at room temperature (40 psi-hydrogen) for 2 hours. The reaction mixture was filtered through celite. The filtrate was evaporated at reduced pressure to give the desired product. Yield—87.5%. Rf—0.5 (Ethyl acetate:Hexane (1:1)

Workup

  1. customwas performed at room temperature
  2. customfor 2 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-2ed56aad8c2146049d5fb89af952f419
Source dataset
uspto-grants-2013_11
Patent number
US08580795B2

Reaction notes

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