Sodium Hydroxide → 5'-(3,7-dimethylocta-2,6-dienyl)-1'-(4-methoxyphenyl)-7',8'-dimethyl-2',4'-dihydro-1'H-spiro[cyclobutane-1,3'-quinolin]-6'ol

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Reaction Steps

To a solution of 1′-(4-methoxyphenyl)-7′,8′-dimethyl-1′,4′-dihydro-2′H-spiro[cyclobutane-1,3′-quinolin]-6′-ol (112 mg) in 3.2 mL t-BuOH was added NaOH (224 μL) and geranyl bromide (133 μL). After 20 minutes, saturated NH4Cl was added and the mixture was extracted with dichloromethane. The organic phase was then washed with brine, dried and evaporated. The residue was passed through a column (Hexane:EtOAc=10:1.2-10:2) to give 5′-(3,7-dimethylocta-2,6-dienyl)-1′-(4-methoxyphenyl)-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinolin]-6′ol (14.7 mg) as a semi white solid. 1H-NMR (300 MHz, CDCl3) δ=6.79-6.62 (m, 4H); 5.26-5.13 (m, 1H); 5.13-5.01 (m, 1H); 4.93 (s, 1H); 3.76 (s, 3H); 3.61 (s, 2H); 2.79 (s, 2H); 2.17-2.02 (m, 7H); 1.82-1.28 (m, 18H). 13C-NMR (75 MHz, CDCl3) δ=152.74, 148.42, 146.18, 138.01, 135.33, 131.98, 129.67, 126.73, 123.86, 122.39, 122.12, 121.95, 119.93, 113.99, 76.63, 61.49, 55.51, 40.16, 39.75, 38.33, 32.89, 26.46, 25.75, 25.53, 17.77, 16.27, 15.76, 15.61, 12.39 ppm.

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