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

HRID 389739Notes

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-f3c362f2d0004c1fa1859baecbe9ff1c
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378095B2

Reaction notes

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