2-Isobutylsuccinic acid-4-t-butyl ester-1-methyl ester → 2-Isobutyl-succinic acid-4-t-butyl ester
Reaction equation
C[O-].[K+].C[O:5][C:6](=[O:20])[CH:7]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>CO>[C:12]([O:11][C:9](=[O:10])[CH2:8][CH:7]([CH2:16][CH:17]([CH3:18])[CH3:19])[C:6]([OH:20])=[O:5])([CH3:15])([CH3:14])[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Potassium methoxide (0.15 g, 2.04 mmol) in methanol (3 mL) was added dropwise to a stirring solution of 2 (0.49 g, 2.04 mmol) in methanol (5 mL) at 0° C. After 10 minutes, the mixture was partitioned between ether (100 mL) and water (50 mL). The ether layer was washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was chromatographed (SiO2, pentane/ether, 98:2) to give the nitro-alkene 3 (0.21 g, 57%) as a pale yellow oil; Rf(heptane/ethyl acetate, 8:2) 0.54; νmax(film)/cm−1 1643 (C═C), 1509 (NO2), 1342 (NO2); δH (400 MHz; CDCl3): 7.12 (1H, quint,J=2.0, CHNO2), 3.01 (1H, ddt, J=20.5, 8.0, 2.1), 2.90 (1H, ddt, J=20.5, 7.3, 2.1), 2.54 (1H, ddt, J=17.8, 7.1, 2.0), 2.43 (1H, ddt, J17.7, 5.6, 1.9), 2.21 (1H, m), 2.12 (1H, m), 1.60–1:24 (8H, m).