Stannane, hydroxytrimethyl- → 2-Iodo-5-(4-methoxyphenyl)oxazole-4-carboxylic acid

HRID 714972Notes

Reaction equation

[I:1][C:2]1[O:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:5]([C:7]([O:9]CC)=[O:8])[N:6]=1.[OH-].C[Sn+](C)C>ClCCCl>[I:1][C:2]1[O:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 2-iodo-5-(4-methoxyphenyl)oxazole-4-carboxylate (1.00 g, 2.7 mmol) in DCE (25 mL) was added trimethyl tin hydroxide (1.70 g, 9.4 mmol) and the resultant mixture stirred at 80° C. for 3 hours. Trimethyl tin hydroxide (0.24 g, 1.3 mmol) was then added and the reaction stirred at 80° C. overnight. The reaction was cooled to room temperature and extracted with DCM. The organic phase was washed with 1M aqueous HCl and brine, dried over MgSO4 and the solvent removed in vacuo to give 2-iodo-5-(4-methoxyphenyl)oxazole-4-carboxylic acid (0.92 g, 2.7 mmol, 99%) as a white solid which was used without further purification. 1H NMR (CDCl3) 3.88 (3H, s), 6.99 (2H, d), 8.13 (2H, d). LCMS (1) Rt: 1.03 min; m/z (ES+) 346.

Workup

temperatureThe reaction was cooled to room temperature
extractionextracted with DCM
washThe organic phase was washed with 1M aqueous HCl and brine
dry with materialdried over MgSO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-268a96153f2e4400a5c14199b77ec494
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187465B2

Reaction notes

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