Methyl 3-(benzyloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate → Methyl 3-hydroxy-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate

HRID 75971Notes

Reaction equation

HRID 75971 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[O:27][C:28]([CH3:31])=[N:29][N:30]=3)=[CH:22][CH:21]=2)[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[O:27][C:28]([CH3:31])=[N:29][N:30]=3)=[CH:24][CH:25]=2)[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 66972395Methyl 3-(benzyloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 66972201Methyl 3-hydroxy-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoateYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a solution of Methyl 3-(benzyloxy)-5-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]benzoate (28 g) (Intermediate 8) in glacial acetic acid, suspension of 10% Pd/C in glacial acetic acid was added in Parr hydrogenation apparatus. The reaction was subjected under 60 PSI of hydrogen for 6 h. After completion, the reaction mixture was filtered to remove catalyst. Filtrate was poured into ice, the solid obtained was filtered, washed with water, saturated sodium bicarbonate solution, water, petroleum ether, air dried to obtain desired product (18 g, 70%).

Workup

  1. additionwas added in Parr hydrogenation apparatus
  2. filtrationAfter completion, the reaction mixture was filtered
  3. customto remove catalyst
  4. additionFiltrate was poured into ice
  5. customthe solid obtained
  6. filtrationwas filtered
  7. washwashed with water, saturated sodium bicarbonate solution, water, petroleum ether, air
  8. customdried

Sources & evidence

ORD record
ord-af312db9e6c74c5eb8420fec35cf519a
Source dataset
uspto-grants-2014_09
Patent number
US08835469B2

Reaction notes

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