Potassium Carbonate → HCID 19874793, compound

HRID 465585Notes

Reaction equation

HRID 465585 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][CH2:19][CH2:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][CH2:19][CH2:20][CH2:21][C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:5][CH2:6][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyran

Product 1

HCID 19874793HCID 19874793, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.0 g (12.8 mmol) ethyl 2-oxocyclopentanecarboxylate, 5.71 g (25.6 mmol) 1-(tetrahydropyranyloxy)-3-bromopropane, 7.08 g (52.2 mmol) powdered potassium carbonate and 60 ml acetone is heated to 60° under nitrogen with stirring for 8 h. The reaction mixture is cooled to room temperature, filtered and evaporated to give a yellow orange liquid which is purified by flash chromatography using 1:9 ethyl acetate/hexane to yield 2-[3-(tetrahydropyranyloxy)propyl]-2-ethoxycarbonylcyclopentanone; IR (neat): 1750, 1724 cm-1.

Workup

  1. temperatureis heated to 60° under nitrogen
  2. filtrationfiltered
  3. customevaporated
  4. customto give a yellow orange liquid which
  5. customis purified by flash chromatography

Sources & evidence

ORD record
ord-9f1c407af67e43b2af30caebe29a876e
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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