2-(5-Methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole → 2-(4,5-Dimethoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole

HRID 2213992Notes

Reaction equation

HRID 2213992 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]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:12]=3[N:13]=2)[CH:8]=1.[CH3:23][O:24]COC1C=CC(C=NC2C(C)=CC=CC=2O)=CC=1>>[CH3:23][O:24][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:12]=3[N:13]=2)=[C:6]([O:19][CH2:20][O:21][CH3:22])[CH:5]=1

Participants

3

Reactant 2

HCID 219593252-(5-Methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazoleHCID 219593272-[(4-Methoxymethoxybenzylidene)amino]-3-methylphenol

Product 1

HCID 219593182-(4,5-Dimethoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole

Procedure

2-(4,5-dimethoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole (F9) was prepared in a similar manner for the preparation of 2-(5-methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole (F8) by using 2-[(4-methoxymethoxybenzylidene)amino]-3-methylphenol (F6) (3.31 g, 10 mmol) instead of 2-[(5-methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol (F4) in 62% (2.07 g): 1H-NMR (400 MHz, CDCl3) δ2.66 (s, 3H), 3.58 (s, 3H), 3.95 (s, 3H), 3.97 (s, 3H), 5.28 (s, 2H), 6.84 (s, 1H), 7.12 (d, 1H, J=8.0 Hz), 7.21 (t, 1H, J=8.0 Hz), 7.39 (d, 1H, J=8.0 Hz), 7.63 (s, 1H).

Sources & evidence

ORD record
ord-f9c657ccb22046d28d0b16c2c22082b3
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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