Potassium Carbonate → HCID 60155620, compound

HRID 1506890Notes

Reaction equation

HRID 1506890 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[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:9][C:7]1[CH:8]=[C:3]([CH2:2][CH:19]2[CH2:20][CH2:21][CH2:22][C:18]2=[O:17])[CH:4]=[C:5]([F:16])[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 117676170HCID 117676170, compound

Product 1

HCID 60155620HCID 60155620, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound (32b) (2.2 g, 7.5 mmol), methyl 2-oxocyclopentane-carboxylate (1.3 mL, 11.3 mmol), and anhydrous potassium carbonate (1.9 g, 13.6 mmol) in acetone (100 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 1.7 g (64%) of compound (33b) 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-ae4aeb4e4ce64559b9af81862bb1ae8b
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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