2-[(5-Methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol → 2-(5-Methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole

HRID 855917Notes

Reaction equation

HRID 855917 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH2:20][O:21][CH3:22])=[C:7]([CH:18]=1)[CH:8]=[N:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[OH:17]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH2:20][O:21][CH3:22])=[C:7]([C:8]2[O:17][C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=3[N:9]=2)[CH:18]=1

Participants

3

Reactant 1

HCID 219593232-[(5-Methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol

Product 1

HCID 219593252-(5-Methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazoleYield 65.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-[(5-methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol (F4) (1.51 g, 5 mmol) and BaMnO4 (5.13 g, 20 mmol) in benzene (50 mL) was refluxed for 5 hours under dry N2 gas flowing. After the reaction mixture was cooled to room temperature, BaMnO4 was removed through Celite and the filtrate was concentrated in vacuo. The black residue was purified by silica gel column chromatography (CHCl3) to afford the objective compound as a pale yellow solid (976 mg, 65%): 1H-NMR (500 MHz, CDCl3) , 2.68 (s, 3H), 3.55 (s, 3H), 3.87 (s, 3H), 5.25 (s, 2H), 7.02 (dd, 1H, J=9.0, 3.0 Hz), 7.15 (d, 1H, J=8.0 Hz), 7.21 (d, 1H, J=9.0 Hz), 7.24 (t, 1H, J=8.0 Hz), 7.42 (d, 1H, J=8.0 Hz), 7.63 (d, 1H, J=3.0 Hz).

Workup

  1. customBaMnO4 was removed through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe black residue was purified by silica gel column chromatography (CHCl3)

Sources & evidence

ORD record
ord-7a412120c8c4496caa07161449c9ad12
Source dataset
uspto-grants-2007_08
Patent number
US07262301B1

Reaction notes

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