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

HRID 722902Notes

Reaction equation

HRID 722902 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; vmax(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-5785516908ee48928a3850f01ed80e5a
Source dataset
uspto-grants-2006_11
Patent number
US07138542B2

Reaction notes

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