Sodium Iodide → 4-(3,5-Dimethylbenzyl)-3,5-heptanedione

HRID 353092

반응식

HRID 353092 반응식
[CH3:1][CH2:2][C:3](=[O:9])[CH2:4][C:5](=[O:8])[CH2:6][CH3:7].[H-].[Na+].[I-].[Na+].[CH3:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[CH2:18]Br>CC(=O)CC>[CH3:14][C:15]1[CH:22]=[C:21]([CH:20]=[C:17]([CH3:18])[CH:16]=1)[CH2:23][CH:4]([C:3](=[O:9])[CH2:2][CH3:1])[C:5](=[O:8])[CH2:6][CH3:7]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 819233,5-HeptanedioneHCID 1413343,5-Dimethylbenzyl bromide

생성물 1

HCID 218770904-(3,5-Dimethylbenzyl)-3,5-heptanedione수율 44.2%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

A solution of 3,5-heptanedione (1.24 ml, 9.13 mmol) in 2-butanone (40 ml) was treated with sodium hydride (60% dispersion in oil) (402 mg, 10.05 mmol) (added in portions) and stirred at room temperature for 10 minutes. Sodium iodide (1.5 g, 10.05 mmol) and then by 3,5-dimethylbenzyl bromide (2.0 g, 10.05 mmol) were added to the reaction mixture which was stirred at room temperature for 18 hours. The solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water (×3). The organic phase was dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with cyclohexane followed by cyclohexane:ethyl acetate (40:1, by volume) to afford the title compound as a yellow oil (995 mg).

후처리

  1. stirringwas stirred at room temperature for 18 hours
  2. concentrationThe solution was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water (×3)
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by flash chromatography on silica gel eluting with cyclohexane

출처 및 근거

ORD 기록
ord-ab3a1917d80c43939eecc3561cd7ad4e
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750230B2

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