6-Methoxy-2-methylbenzoxazole → (E)-2-[2-(4-chloropropoxyphenyl)ethenyl]-6-methoxybenzoxazole

HRID 1723511Notes

Reaction equation

HRID 1723511 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[CH3:14][O:15][C:16]1[CH:25]=[CH:24][C:19]2[N:20]=[C:21]([CH3:23])[O:22][C:18]=2[CH:17]=1>>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9](/[CH:10]=[CH:23]/[C:21]2[O:22][C:18]3[CH:17]=[C:16]([O:15][CH3:14])[CH:25]=[CH:24][C:19]=3[N:20]=2)=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 903296-Methoxy-2-methylbenzoxazoleHCID 35514794-(3-Chloropropoxy)-benzaldehyde

Product 1

HCID 14146345(E)-2-[2-(4-chloropropoxyphenyl)ethenyl]-6-methoxybenzoxazoleYield 69%

Procedure

The procedure of Example 8 was followed starting with 4-chloropropoxybenzaldehyde of Example 8 (1.9 g, 10 mmol) and using 6-methoxy-2-methylbenzoxazole in place of 2-methylbenzoxazole (1.6 ml, 10 mmol) to give 2.4 g (69% yield) of (E)-2-[2-(4-chloropropoxyphenyl)ethenyl]-6-methoxybenzoxazole as an amber oil. 1H NMR (CDCl3): δ 8.29-6.99 (m, 9H), 4.22 (t, J=5.4 Hz, 2H), 3.93 (s, 3H), 3.24 (m, 2H), 2.51 (m, 2H).

Sources & evidence

ORD record
ord-be6b764fd0a94831837f19a2ede1a0c9
Source dataset
uspto-grants-1989_08
Patent number
US04861897

Reaction notes

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