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

HRID 2213991Notes

Reaction equation

HRID 2213991 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-methylbenzoxazole

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 soild (976 mg, 65%): 1H-NMR (500 MHz, CDCl3) δ2.68 (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)
  4. customto afford the objective compound as a pale yellow soild (976 mg, 65%)

Sources & evidence

ORD record
ord-f499309cc339450a9d10f500e5109181
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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