2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazole → 2-Ethyl-4-[5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazol-2-yl]-6-methyl-phenol

HRID 1666598Notes

Reaction equation

HRID 1666598 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]([CH3:30])[CH3:29])=[C:23]([CH3:31])[CH:22]=3)=[N:19][N:20]=2)=[CH:11][C:10]=1[CH2:32][CH3:33])C1C=CC=CC=1>C1COCC1.CCO.[Pd]>[CH2:32]([C:10]1[CH:11]=[C:12]([C:16]2[O:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]([CH3:29])[CH3:30])=[C:23]([CH3:31])[CH:22]=3)=[N:19][N:20]=2)[CH:13]=[C:14]([CH3:15])[C:9]=1[OH:8])[CH3:33]

Participants

5

Reactant 1

HCID 674468842-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazole

Product 1

HCID 1360852372-Ethyl-4-[5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazol-2-yl]-6-methyl-phenolYield 79.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazole (1.25 g, 2.82 mmol) in THF (10 mL), Pd/C (100 mg, 10% Pd) in EtOH (10 mL) is added. The mixture is stirred at rt under 1 atmosphere of H2 for 16 h before the catalyst is removed by filtration. The filtrate is concentrated and separated by CC on silica gel eluting with heptane:EA 4:1 to 1:1 to give 2-ethyl-4-[5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazol-2-yl]-6-methyl-phenol (0.79 g) as a greenish solid; LC-MS: tR=1.12 min, [M+1]+=353.17, 1H NMR (D6-DMSO): δ 9.02 (s br, 1H), 7.90-7.86 (m, 2H), 7.70-7.66 (m, 2H), 7.13 (d, J=9.4 Hz, 1H), 4.72 (hept, J=5.0^9 Hz, 1H), 2.65 (q, J=7.6 Hz, 2H), 2.26 (s, 3H), 2.20 (s, 3H), 1.31 (d, J=5.9 Hz, 6H), 1.17 (t, J=7.6 Hz, 3H).

Workup

  1. customis removed by filtration
  2. concentrationThe filtrate is concentrated
  3. customseparated by CC on silica gel eluting with heptane:EA 4:1 to 1:1

Sources & evidence

ORD record
ord-d6184bdb47294e3392b1826d60516e72
Source dataset
uspto-grants-2011_10
Patent number
US08044076B2

Reaction notes

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