Sodium Hydroxide → 2-((1-(Trifluoromethyl)cyclopropyl)methyl)malonic acid

HRID 1049282Notes

Reaction equation

HRID 1049282 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1([CH2:6][CH:7]([C:14]([O:16]C(C)C)=[O:15])[C:8]([O:10]C(C)C)=[O:9])[CH2:5][CH2:4]1.[OH-].[Na+]>CO.O1CCOCC1.O>[F:1][C:2]([F:20])([F:21])[C:3]1([CH2:6][CH:7]([C:14]([OH:16])=[O:15])[C:8]([OH:10])=[O:9])[CH2:5][CH2:4]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 90403930Diisopropyl 2-((1-(trifluoromethyl)cyclopropyl)methyl)malonate

Product 1

HCID 904024822-((1-(Trifluoromethyl)cyclopropyl)methyl)malonic acidYield 101.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of diisopropyl 2-((1-(trifluoromethyl)cyclopropyl)methyl)malonate (1.53 g, 4.93 mmol) in MeOH (10 mL), dioxane (10 mL) and H2O (10 mL) was treated with NaOH (1.183 g, 29.6 mmol) and heated at 40° C. overnight. The mixture was cooled to RT, the organics removed under reduced pressure, the aqueous residue acidified with 3M HCl, extracted with DCM and the combined organics were dried over Na2SO4 and concentrated to dryness to afford 2-((1-(trifluoromethyl)cyclopropyl)methyl)malonic acid (1.13 g, 101%). 1H NMR (400 MHz, DMSO-d6): δ 12.91 (s, 2H), 3.36-3.34 (t, J=7.09 Hz, 1H), 2.08 (d, J=7.0 Hz, 2H), 0.88 (m, 2H), 0.77 (m, 2H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. customthe organics removed under reduced pressure
  3. extractionextracted with DCM
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3af87404ad1a49a9a480ec21cd80d605
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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