Water → 1-Isopropyl-3-oxocyclopentanecarboxylic acid

HRID 643524Notes

Reaction equation

HRID 643524 reaction equation
[CH:1]([C:4]1([C:13]([O:15]C(C)(C)C)=[O:14])[CH2:8][CH2:7][C:6](OC)([O:9]C)[CH2:5]1)([CH3:3])[CH3:2].O>Cl.O1CCOCC1>[CH:1]([C:4]1([C:13]([OH:15])=[O:14])[CH2:8][CH2:7][C:6](=[O:9])[CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 58987981Tert-butyl 1-isopropyl-3,3-dimethoxycyclopentanecarboxylate

Product 1

HCID 186143931-Isopropyl-3-oxocyclopentanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 1-isopropyl-3,3-dimethoxycyclopentanecarboxylate (8.32 g, 30.5 mmol) was dissolved in 4N anhydrous HCl in dioxane (50 mL) and water (10 mL) was added. The reaction mixture was stirred at rt overnight, then was concentrated. The residue was dissolved in DCM, dried over anhydrous MgSO4, filtered, and concentrated to give 1-isopropyl-3-oxocyclopentanecarboxylic acid (used without purification). 1H NMR (500 MHz, CDCl3) δ 2.70 (d, J=18.1 Hz, 1H), 2.44-2.39 (m, 1H), 2.30-2.15 (m, 2H), 2.14 (dd, J=18.1, 1.0 Hz, 1H), 2.06 (p, J=6.9 Hz, 1H), 1.98 (m, 1H), 0.98 (dd, J=11.4, 6.9 Hz, 6H).

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in DCM
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-41a92522ec5e441b85c9c13df7818ec8
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

Loading…