N(C(C)C)[CH:2](C)C.[Li]CCCC.[CH3:13][O:14][C:15]([CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([O:27][CH3:28])[CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:16].CI.[NH4+].[Cl-]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH3:13][O:14][C:15]([C:17]1([CH3:2])[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([O:27][CH3:28])[CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:16]To iPr2NH (202 mg, 2.0 mmol) in THF (1.0 mL) was added BuLi (2.5 M, 0.8 mL, 2.0 mmol) at −78° C. After 10 minutes, 8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester in THF (1.0 mL) was added and the reaction mixture turned yellow. Methyl iodide (568 mg, 4.0 mmol) and HMPA (1.0 mL) were added after 30 minutes. The reaction mixture was allowed to stir at −78° C. for 3 hours at ambient temperature before aqueous NH4Cl was added. The mixture was extracted with ethyl acetate (3×20 mL) and the combined extracts were dried over MgSO4 and purified by column chromatography to give 8-methoxy-2-methyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester (170 mg, 84%).
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