Triethylamine → 1-(4-Fluorophenyl)1,4-hexanedione

HRID 5716

Reaction equation

HRID 5716 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]([C:12]([CH2:14][CH3:15])=[O:13])=[CH2:11].C(N(CC)CC)C>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[O:7])[CH2:11][CH2:10][C:12](=[O:13])[CH2:14][CH3:15])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 153941-Penten-3-oneHCID 680234-Fluorobenzaldehyde

Product 1

HCID 110958221-(4-Fluorophenyl)1,4-hexanedioneYield 89.5%

Reagents, catalysts & solvents 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 36.61 g (295 mmol) of 4-fluorobenzaldehyde, 25 g (297.2 mmol) of ethyl vinyl ketone, 29 mL (206.9 mmol) of triethylamine and 11.94 g (44.25 mmol) of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride is stirred and heated at 70° C. for six hours. The cooled solution is diluted with 2 liters of diethylether and washed with 2×300 mL of water, 2×100 mL of 2M hydrochloric acid, 100 mL of water, 200 mL of a saturated solution of sodium bicarbonate and brine. The organic layer is separated, dried (magnesium sulfate), filtered, and concentrated to provide 55 g of 1-(4-fluorophenyl)-1,4-hexanedione after recrystallization from methanol; mp 56°-57° C.

Workup

  1. washwashed with 2×300 mL of water, 2×100 mL of 2M hydrochloric acid, 100 mL of water, 200 mL of a saturated solution of sodium bicarbonate and brine
  2. customThe organic layer is separated
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2c45a2c2970649979f6c2d88874662a4
Source dataset
uspto-grants-1993_09
Patent number
US05245047

Linked notes

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