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

HRID 2300601

반응식

HRID 2300601 반응식
[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

참가 물질

5

반응물 3

HCID 7166BenzoylacetoneHCID 125271-IodohexaneHCID 2724682Lithium diisopropylamide

생성물 1

HCID 1116961,3-Decanedione, 1-phenyl-

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-4905cd4da37b43e6bbf76ffe0d8f79bb
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498174B1

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