Potassium Carbonate → HCID 19884778, compound

HRID 846233Notes

Reaction equation

HRID 846233 reaction equation
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:27])[C:20]([CH3:26])([CH3:25])[CH2:21][C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2].[C:34](=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:27])[C:20]([CH3:26])([CH3:25])[CH2:21][C:22]([O:24][CH3:34])=[O:23])=[CH:15][CH:14]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19884729HCID 19884729, compound

Product 1

HCID 19884778HCID 19884778, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of the product from Step C (250 mg), 4-(3-bromopropyl)-2-hydroxy-3-propylacetophenone (315 mg), and potassium carbonate (410 mg) in methyl ethyl ketone (10 ml) was refluxed under N2 for 4 hours then stirred at ambient temperature for 18 hours. The mixture was filtered, washed with brine, evaporated to dryness and the resulting oil was Purified by chromatography on silica gel to provide the title compound as an oil. NMR (CDCl3) 0.90 (3H, t), 1.43 (6H, s), 1.52 (2H, m), 2.30 (2H, m), 2.50 (3H, s), 2.55 (2H, m), 2.75 (2H, s), 3.57 (3H, s), 4.18 (4H, m), 6.41 (1H, d), 6.88 (2H, d), 7.53 (1H, d), 7.72 (2H, d).

Workup

  1. temperaturewas refluxed under N2 for 4 hours
  2. filtrationThe mixture was filtered
  3. washwashed with brine
  4. customevaporated to dryness
  5. customthe resulting oil was Purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7246ceb0b7764572bf27fabdc59ab40b
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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