Allyl Alcohol → 2-(5-Nitro-2-allyloxyphenyl)-5-phenylbenzoxazole

HRID 722531Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[O:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][C:14]=2[N:15]=1.[CH2:26]([OH:29])[CH:27]=[CH2:28]>>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:29][CH2:26][CH:27]=[CH2:28])=[C:3]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][C:14]=3[N:15]=2)[CH:4]=1)([O-:10])=[O:9]

Participants

Reactant 2

HCID 7858Allyl Alcohol

HCID 218843342-(2-Fluoro-5-nitrophenyl)-5-phenylbenzoxazole

Product 1

HCID 218845392-(5-Nitro-2-allyloxyphenyl)-5-phenylbenzoxazole

Procedure

Prepared by the method of Example 44a), from 2-(2-fluoro-5-nitrophenyl)-5-phenylbenzoxazole (200 mg, 0.6 mmol) and allyl alcohol (4 ml) the subtitle compound was obtained (216 mg, 97%). 1H NMR (DMSO) δ 8.83(d, 1H), 8.38(dd, 1H), 8.06(d, 1H), 7.82(d, 1H), 7.69(m, 3H), 7.44(t, 3H), 7.33(t, 1H), 6.08(m, 1H), 5.60(dd, 1H), 5.30(dd, 1H), 4.90(m, 2H).

Sources & evidence

ORD record: ord-8160729eee22433d95f55f83a683d2da
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138425B2

Reaction notes

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