Benzoylacetone → 1,3-Decanedione, 1-phenyl-

HRID 2300601Notes

Reaction equation

[C:1]([CH2:9][C:10](=[O:12])[CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.I[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C1COCC1>[C:2]1([C:1](=[O:8])[CH2:9][C:10](=[O:12])[CH2:11][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1 g (6.1 mmol) of benzoylacetone in 6 mL of THF at −78° C. was added 8.2 mL (12.3 mmol) of a 1.5 M LDA solution in THF. Warmed to 0° C. over 2 h, then 2.6 mL (12.3 mmol) of 1-iodohexane was added. The mixture was stirred at rt for 3 h before quenching with saturated aqueous NH4Cl solution and dilution with Et2O. The organics were dried (Na2SO4), filtered, concentrated, and purified by silica gel chromatography (15/1 hexanes/Et2O) to yield Intermediate 19: TLC Rf=0.52 (1/10 Et2O/Hexanes); 1H NMR (400 MHz, CDCl3, enol form) δ7.88 (m, 2H), 7.54-7.43 (m, 3H), 6.17 (s, 1H), 2.42 (t, 2H, J=7.6), 1.66 (m, 2H), 1.4-1.25 (m, 8H), 0.85 (m, 3H); low resolution MS(ES+) m/e 269.0 (M+Na+).

Workup

custombefore quenching with saturated aqueous NH4Cl solution and dilution with Et2O
dry with materialThe organics were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
custompurified by silica gel chromatography (15/1 hexanes/Et2O)

Sources & evidence

ORD record: ord-4905cd4da37b43e6bbf76ffe0d8f79bb
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498174B1

Reaction notes

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