Triethylamine → HCID 14100418, compound

HRID 648465Notes

Reaction equation

HRID 648465 reaction equation
[CH3:1][CH:2]([CH3:17])[C:3]([C:5](=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)C(OC)=O)=[O:4].C(N(CC)CC)C.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1.[OH-].[Na+]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.O1CCCC1.O>[F:25][C:26]1[CH:33]=[CH:32][C:29]([C:30](=[O:31])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:5][C:3](=[O:4])[CH:2]([CH3:1])[CH3:17])=[CH:28][CH:27]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 680234-FluorobenzaldehydeHCID 85558854HCID 85558854, compound

Product 1

HCID 14100418HCID 14100418, compoundYield 36.4%

Reagents, catalysts & solvents 4

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 15.4 g (66 mmol) of 2-(2-methyl-1-oxopropyl)-3-(2-pyridinyl)propenoic acid, methyl ester, 6.5 ml (46.2 mmol) of triethylamine and 8.2 g (66 mmol) of 4-fluorobenzaldehyde was added 15 mole percent of 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium chloride (Aldrich Chemical Co., Milwaukee, WI, USA). The resulting mixture was heated at 70° C. for 3 hours, cooled, dissolved in ethyl acetate and washed successively with brine and water. The organic layer was separated, dried to yield the crude products an oil. The material was redissolved in 300 ml of tetrahydrofuran, and 150 ml of water and 6.6 g (165 mmol) of sodium hydroxide were added. This mixture was vigorously stirred overnight, concentrated, and the residue dissolved in a mixture of diethyl ether and ethyl acetate. The extract was washed with water and then extracted with 2M hydrochloric acid. The acid extract was made alkaline and extracted with diethyl ether. The ether extract was evaporated to yield 7.2 g (36%) of 1-(4-fluorophenyl)-5-methyl-2-(2-pyridinyl)hexane-1,4-dione.

Workup

  1. temperaturecooled
  2. washwashed successively with brine and water
  3. customThe organic layer was separated
  4. customdried
  5. customto yield the crude products an oil
  6. concentrationconcentrated
  7. dissolutionthe residue dissolved in a mixture of diethyl ether and ethyl acetate
  8. washThe extract was washed with water
  9. extractionextracted with 2M hydrochloric acid
  10. extractionThe acid extract
  11. extractionextracted with diethyl ether
  12. extractionThe ether extract
  13. customwas evaporated

Sources & evidence

ORD record
ord-ec5ba511dc324cee9c19b8cb9ee5c95d
Source dataset
uspto-grants-1988_04
Patent number
US04735958

Reaction notes

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