2-Isobutylsuccinic acid-4-t-butyl ester-1-methyl ester → 2-Isobutyl-succinic acid-4-t-butyl ester

HRID 458071Notes

Reaction equation

HRID 458071 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

HCID 218883142-Isobutylsuccinic acid-4-t-butyl ester-1-methyl esterHCID 23664618Potassium methoxide

Product 1

HCID 99427122-Isobutyl-succinic acid-4-t-butyl esterYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

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).

Workup

  1. customthe mixture was partitioned between ether (100 mL) and water (50 mL)
  2. washThe ether layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was chromatographed (SiO2, pentane/ether, 98:2)

Sources & evidence

ORD record
ord-6bdf7f5647e24ddd9d282b5fa8f1bfb0
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

Loading…