Potassium Carbonate → HCID 60155619, compound

HRID 1506889Notes

Reaction equation

HRID 1506889 reaction equation
Br[CH2:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([CH:10]([CH3:15])[C:11]([O:13]C)=[O:12])=[C:5]([F:16])[CH:4]=1.[O:17]=[C:18]1[CH2:22][CH2:21][CH2:20][CH:19]1C(OC)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:16][C:5]1[CH:4]=[C:3]([CH2:2][CH:19]2[CH2:20][CH2:21][CH2:22][C:18]2=[O:17])[C:8]([F:9])=[CH:7][C:6]=1[CH:10]([CH3:15])[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 60155618HCID 60155618, compound

Product 1

HCID 60155619HCID 60155619, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound (32a) (4.8 g, 16.4 mmol), methyl 2-oxocyclo-pentanecarboxylate (2.5 mL, 21.9 mmol), and anhydrous potassium carbonate (4.0 g, 28.9 mmol) in acetone (200 mL) were allowed to react in the same manner as in Example 15. The obtained crude product was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution followed by conventional decarboxylation and hydrolysis to give 3.5 g (60%) of compound (33a) of interest as clear yellow oil.

Workup

  1. customto react in the same manner as in Example 15
  2. customThe obtained crude product
  3. washwas subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution
  4. customfollowed by conventional decarboxylation and hydrolysis

Sources & evidence

ORD record
ord-016061e9ef09404b8f1eb7043fc3447e
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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