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 2098331Notes

Reaction equation

HRID 2098331 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>C(O)(=O)C>[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

3

Reactant 1

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

Product 1

HCID 66972201Methyl 3-hydroxy-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoateYield 76.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl 3-(benzyloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate (28 g, 72.1 mmol, 1 equiv.) (Intermediate 9) was debenzylated in acetic acid using 10% Pd/C (5.6 g) at 60 PSI in hydrogenation apparatus. After complete reaction, the reaction mixture was poured on ice and the solid obtained was filtered through Buckner funnel. The solid was washed with water and air-dried to furnish the title compound (18 g).

Workup

  1. customAfter complete reaction
  2. additionthe reaction mixture was poured on ice
  3. customthe solid obtained
  4. filtrationwas filtered through Buckner funnel
  5. washThe solid was washed with water
  6. customair-dried

Sources & evidence

ORD record
ord-2d409a0c97d44ffcbda8d3470508728c
Source dataset
uspto-grants-2013_05
Patent number
US08450494B2

Reaction notes

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