Water → HCID 67953936, compound

HRID 238348Notes

Reaction equation

HRID 238348 reaction equation
[F:1][C:2]1([F:17])[CH2:6][CH2:5][C@@H:4]([C:7]([O:9]CC2C=CC=CC=2)=[O:8])[CH2:3]1.[Li+].[OH-].O>CO>[F:1][C:2]1([F:17])[CH2:6][CH2:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86666594HCID 86666594, compound

Product 1

HCID 67953936HCID 67953936, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-benzyl 3,3-difluorocyclopentanecarboxylate (13 g, 54.1 mmol) was dissolved in MeOH (200 mL) at room temperature with stirring then 0.5 M LiOH (216 mL, 108 mmol) was added. After stirring for 2 h, water was added to the reaction mixture and concentrated to remove volatile solvents. The aqueous layer was rinsed with Et2O (2×) then acidified to pH 3 with 1N HCl. The aqueous layer was extracted with methylene chloride (2×) and the organic layers were combined, dried (Na2SO4), and concentrated to give (R)-3,3-difluorocyclopentanecarboxylic acid (6.58 g, 43.8 mmol, 81% yield) as an oil. 1H NMR (MeOD3, 400 MHz) δ 3.03 (m, 1H), 2.33 (m, 2H), 1.95-2.20 (m, 4H); m/z=149.2 (M−H).

Workup

  1. stirringAfter stirring for 2 h
  2. concentrationconcentrated
  3. customto remove volatile solvents
  4. washThe aqueous layer was rinsed with Et2O (2×)
  5. extractionThe aqueous layer was extracted with methylene chloride (2×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-657c5ba29df9453aac058208ab5cedec
Source dataset
uspto-grants-2014_02
Patent number
US08642622B2

Reaction notes

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