2-(2,3-dimethoxyphenyl)-4,4-dimethyl-5H-1,3-oxazole

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using the method of example 44, steps 1-3, with 2-(2,3-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline (J. Org. Chem. 43, 1372 (1978) and the Grignard reagent prepared from 1-bromo-2-(3-thiophenyl)ethane and magnesium the title compound was prepared and the structure confirmed by NMR spectroscopy. 4. 3-[2-(2-Bromomethyl-6-methoxy-phenyl)-ethyl]-thiophene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isopropylmagnesium chloride (2.0M in diethyl ether) (18.75 ml, 37.5 mmol) was added dropwise to a solution of 2-(2,3-dimethoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (7.06 g, 30.0 mmol) in freshly distilled tetrahydrofuran at room temperature. The mixture was stirred overnight, quenched with water, and diluted with diethyl ether. The layers were separated, and the aqueous layer was washed twice with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by silica gel flash chromatography, eluting with hexane/ethyl acetate, gave 2-(2-isopropyl-3-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole as a clear oil (7.08 g, 95.4%). quenched with water diluted with diethyl ether The layers were separated the aqueous layer was washed twice with diethyl ether The combined organic extracts were dried over anhydrous sodium sulfate concentrated in vacuo Purification by silica gel flash chromatography eluting with hexane/ethyl acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using the method of example 44, steps 1-3, with 2-(2,3-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline (J. Org. Chem. 43, 1372 (1978) and the Grignard reagent prepared from 1-bromo-2-(3-thiophenyl)ethane and magnesium the title compound was prepared and the structure confirmed by NMR spectroscopy. 4. 3-[2-(2-Bromomethyl-6-methoxy-phenyl)-ethyl]-thiophene