2-((1-(Trifluoromethyl)cyclopropyl)methyl)malonic acid → 3-(1-(Trifluoromethyl)cyclopropyl)propanoic acid

HRID 1049283Notes

Reaction equation

HRID 1049283 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1([CH2:6][CH:7](C(O)=O)[C:8]([OH:10])=[O:9])[CH2:5][CH2:4]1>N1C=CC=CC=1>[F:1][C:2]([F:14])([F:15])[C:3]1([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH2:5][CH2:4]1

Participants

3

Reactant 1

HCID 904024822-((1-(Trifluoromethyl)cyclopropyl)methyl)malonic acid

Product 1

HCID 904029993-(1-(Trifluoromethyl)cyclopropyl)propanoic acidYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-((1-(trifluoromethyl)cyclopropyl)methyl)malonic acid (1.13 g, 5.00 mmol) in pyridine (25 mL) was heated at 100° C. overnight, cooled to RT and concentrated to dryness. The residue was dissolved in 3N HCl, extracted with DCM (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford 3-(1-(trifluoromethyl)cyclopropyl)propanoic acid (664 mg, 73%). 1H NMR (400 MHz, DMSO-d6): δ 12.18 (s, 1H), 2.32 (t, J=8.0 Hz, 2H), 1.79 (t, J=8.0 Hz, 2H), 0.86 (m, 2H), 0.75 (m, 2H).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in 3N HCl
  3. extractionextracted with DCM (3×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-00e58a89e8284c1fb93dbce315da2889
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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