Carbon Dioxide → 8-methoxy-3,4-dihydro-1H-naphthalene-2,2-dicarboxylic acid methyl ester

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Reaction Steps

A THF (1.0 mL) solution of 8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester (660 mg, 3.0 mmol) was added to freshly made LDA (made by addition of 2.0 mL of 2.3 M BuLi to 1.5 mL THF solution of 0.7 mL iPr2NH) at −78° C. and the mixture was allowed to stir for 1.5 hour. A CO2 balloon was then applied. The reaction mixture was quenched with aqueous NH4Cl and the resulting mixture was extracted with ethyl acetate (3×15 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to provide the crude-8-methoxy-3,4-dihydro-1H-naphthalene-2,2-dicarboxylic acid methyl ester (470 mg).

Provenance & Evidence