Potassium Hydroxide → HCID 22237562, compound

Participants

Reaction Steps

To a suspension of 4-[3,5,3″,5″-Tetramethyl-5′-(7-phenyl-heptylcarbamoyl)-[1,1′:3′,1″]terphenyl-2′-yloxy]-butyric acid ethyl ester (170 mg, 0.256 mmol) in 4 mL MeOH/1 mL H2O was added solid KOH (12 mg, 0.213 mmol). The reaction mixture was refluxed for 2 d and then the reaction mixture was diluted with 2N HCl and water. The aqueous solution was extracted with EtOAc (3×) and the combined organic extracts were dried over Na2SO4. The solvent was removed in vacuo to give an oil that was flash chromatographed (10% EtOAc:90% Hexanes) on silica gel to yield 70 mg, 43% of the acid as an oily white foam. mp 64-66″C; 1H NMR (DMSO-d6) δ1.29-1.30 (m, 6H); 1.32-1.39 (m, 2H); 1.46-1.48 (m, 4H); 1.86 (t, J=7.47 Hz, 2H); 2.33 (s, 12H); 2.53 (t, J=7.58 Hz, 2H); 3.19-3.31 (m, 4H); 7.01 (s, 2H); 7.12-7.16 (m, 3H); 7.17-7.19 (m, 4H); 7.21-7.24 (m, 2H) 7.71 (s, 2H); 8.48 (t, J=7.00 Hz, 1H); 11.86 (s, 1H); IR 3325, 2925, 2875, 1710, 1630, 1600, 1535, 1450, 1290, 1225, 1210, 850, and 700 cm−1; mass spectrum [(+)APCI], m/z 606 [M+H]+; Anal Calcd. for C40H47NO4: C, 79.30; H, 7.82; N, 2.31; Found: C, 78.65; H, 7.86; N, 1.87.

Provenance & Evidence