[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:13]COC)[CH:5]=1)([CH3:3])[CH3:2].[C:17](Cl)(=O)C.Cl.C[Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO.CCCCCC>[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:17])=[O:9])=[C:6]([OH:13])[CH:5]=1)([CH3:3])[CH3:2]
The 4-isopropyl-2-methoxymethoxybenzoic acid (5.3 g, 23.6 mmol) was dissolved in methylene chloride (75 mL) and MeOH (75 mL). Acetyl chloride (1 mL) was added to generate HCl. The reaction mixture was stirred for 2 h. The reaction was washed with water (2×150 mL), dried (MgSO4), and concentrated under vacuum. The crude product was dissolved in methylene chloride (100 mL) and MeOH (30 mL), and to this solution a 2 M hexane solution of trimethylsilyldiazomethane (11.8 mL, 23.6 mmol) was added dropwise. After 1 h, the solvent was removed under vacuum, giving the title compound as an oil.
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