Sulfuric Acid → 4-(4-Bromo-2-ethylphenyl)-2,6-diethyl-2,6-dimethylpyran-3,5-dione

HRID 341672노트

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HRID 341672 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:10]3([C:14](=[O:15])[C:13]([CH2:17][CH3:18])([CH3:16])[O:12][C:11]3([CH2:20][CH3:21])[CH3:19])[O:9]2)=[C:4]([CH2:22][CH3:23])[CH:3]=1.S(=O)(=O)(O)O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:14](=[O:15])[C:13]([CH2:17][CH3:18])([CH3:16])[O:12][C:11]([CH2:20][CH3:21])([CH3:19])[C:10]2=[O:9])=[C:4]([CH2:22][CH3:23])[CH:3]=1

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 595627242-(4-Bromo-2-ethylphenyl)-4,6-diethyl-4,6-dimethyl-1,5-dioxaspiro[2.4]heptan-7-one

생성물 1

HCID 687339294-(4-Bromo-2-ethylphenyl)-2,6-diethyl-2,6-dimethylpyran-3,5-dione수율 13.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
7.5 °C

실험 절차

To an ice cold solution of 2-(4-bromo-2-ethylphenyl)-4,6-diethyl-4,6-dimethyl-1,5-dioxaspiro[2.4]heptan-7-one (15 g, 0.0397 mol) in dichloromethane (7.5 ml) is added concentrated sulphuric acid (45 ml), dropwise over 50-60 minutes, maintaining the temperature of the reaction mixture at 5-10° C. The reaction mixture is maintained at 5-10° C. for 10-15 minutes, quenched into crushed ice (225 g) and extracted with dichloromethane (3×100 ml). The organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-(4-bromo-2-ethylphenyl)-2,6-diethyl-2,6-dimethylpyran-3,5-dione (2 g) as a white solid.

후처리

  1. temperatureThe reaction mixture is maintained at 5-10° C. for 10-15 minutes
  2. customquenched
  3. custominto crushed ice (225 g)
  4. extractionextracted with dichloromethane (3×100 ml)
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe mixture is filtered
  8. customthe filtrate is evaporated under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-df99c1ae7da04a8588d08dd1553b2b60
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895761B2

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