7-methyl-2-benzofuran-1(3H)-one → 2-{3-[2-(4-Fluorophenyl)oxazol-4-ylmethoxy]phenoxymethyl}-6-methylbenzoic acid

HRID 731131Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:9](=[O:10])[O:8][CH2:7]2.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:20][CH:21]=[C:22]([CH2:24][O:25][C:26]3[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=3)[N:23]=2)=[CH:15][CH:14]=1.C[O-].[Na+]>CN1C(=O)CCC1>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[O:20][CH:21]=[C:22]([CH2:24][O:25][C:26]3[CH:27]=[C:28]([CH:29]=[CH:30][CH:31]=3)[O:32][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[C:6]([CH3:7])[C:11]=3[C:9]([OH:10])=[O:8])[N:23]=2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 130 °C

Procedure

1 g (6.8 mmol) of 7-methylphthalide and 2 g (7.0 mmol) of 3-[2-(4-fluorophenyl)oxazol-4-ylmethoxy]phenol are dissolved in NMP. 3.9 ml of methanolic sodium methoxide (30% strength) are added, the methanol is distilled off, and the mixture is heated to 130° C. No formation of 2-{3-[2-(4-fluorophenyl)oxazol-4-ylmethoxy]phenoxymethyl}-6-methyl-benzoic acid is observed. The 3-[2-(4-fluorophenyl)oxazol-4-ylmethoxy]phenol decomposes.

Workup

distillationthe methanol is distilled off

Sources & evidence

ORD record: ord-ea1319b7318c4eec9b820149a77944ff
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582794B2

Reaction notes

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