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With sodium hydride In tetrahydrofuran at 0 - 20℃; for 9 h; Inert atmosphere
General procedure: To a round-bottom flask that was flame-dried and cooled under nitrogen were added allylic alcohol 51 (0.5 mmol) and THF (2.5 mL). After stirring at 0 °C for 5 min, NaH powder (1 mmol, 2 equiv) was added in one portion, the mixture was then allowed to warm to room temperature. The reaction was quenched by addition of saturated NH4Cl (2 mL) after the indicated time, extracted with EtOAc (10 mL.x.2), and washed by brine (15 mL). The combined organic phase was dried over MgSO4, the solvent was removed under vacuum, and the residue was purified by flash chromatography on silica gel to give the desired ketone product 52.
The product so obtained was reacted with ethyl 2-thiazolyl ketone using the procedure described in Example 4 except that the lithiation step and addition of the above mentioned ketone were conducted at -110 C. The mixture was stirred at -110 C. for 30 minutes and then allowed to warm to -20 C. The mixture was poured into a saturated aqueous ammonium chloride solution. The remaining procedure was as described in Example 4. There was thus obtained the required starting material as an oil in 42% yield. jj. The product gave the following NMR data: (CDCl3 delta values) 0.8 (t, 3H), 2.4 (m, 1H), 2.7 (m, 1H), 3.2 (s, 3H), 3.85 (s, 3H), 5.1 (s, 2H), 6.8 (d, 1H), 6.9 (d, 1H), 7.0 (d, 1H), 7.25 (d, 1H), 7.3-7.45 (m, 5H). 7.7 (d, 1H). The 2-[1-(4-benzyloxy-3-methoxyphenyl)-1-hydroxypropyl]thiazole used as a starting material was obtained as follows: Benzyl bromide was reacted with <strong>[617-05-0]ethyl vanillate</strong> using the conditions described in Example 1 to give ethyl 4-benzyloxy-3-methoxybenzoate in 97% yield m.p. 72-74 C. Following the procedures described in the portion of Example 6 which is concerned with the preparation of starting materials the product so obtained was reacted with thiazol-2-yl-lithium and the resultant product was reacted with ethylmagnesium iodide to give the required starting material as an oil in 20% yield.
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