HCID 67125768, compound → HCID 49834134, compound

HRID 1614866Notes

Reaction equation

HRID 1614866 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14]2)=[CH:9][CH:8]=1)C>CCO.[OH-].[Na+]>[O:18]=[C:15]1[CH2:16][CH2:17][C@@H:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:19])=[O:3])=[CH:8][CH:9]=2)[CH2:14]1

Participants

4

Reactant 1

HCID 67125768HCID 67125768, compound

Product 1

HCID 49834134HCID 49834134, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid ethyl ester (preparation 30) (6.0 mmol, 1.57 g) was taken up in EtOH (6 mL) and NaOH (2N, 6 mL), the reaction mixture stirred at r.t. for 2 h. Then the EtOH was evaporated and the reaction mixture diluted with water, then neutralized with HCl (2N) to pH 5 and extracted with DCM. Dried over Na2SO4 and concentrated in vacuo to yield the title compound (1.24 g, 89%). 1H NMR (300 MHz, CDCl3) δ 7.23-7.06 (m, 2H), 6.98-6.72 (m, 2H), 4.66 (s, 2H), 3.53-3.13 (m, 1H), 2.64 (dd, J=7.5, 18.2, 1H), 2.56-2.17 (m, 4H), 2.14-1.69 (m, 1H).

Workup

  1. customThen the EtOH was evaporated
  2. additionthe reaction mixture diluted with water
  3. extractionextracted with DCM
  4. dry with materialDried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2652b915713a485b932df9e5bffba0be
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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