Sodium Bicarbonate → (5R,6S)-3-oxo-5-(2,2,2-trichloroethoxycarbonyl-oxy)-2,2,6-trimethyl-8-nonenal

HRID 348260노트

반응식

HRID 348260 반응식
C([O:4][CH:5](OC(C)C)[C:6]([CH3:26])([CH3:25])[C:7](=[O:24])[CH2:8][C@@H:9]([O:15][C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[O:17])[C@@H:10]([CH3:14])[CH2:11][CH:12]=[CH2:13])(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1COCC1.O>[O:24]=[C:7]([CH2:8][C@@H:9]([O:15][C:16]([O:18][CH2:19][C:20]([Cl:21])([Cl:22])[Cl:23])=[O:17])[C@@H:10]([CH3:14])[CH2:11][CH:12]=[CH2:13])[C:6]([CH3:26])([CH3:25])[CH:5]=[O:4]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86586619(5R,6S)-1,1-diisopropoxy-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,6-trimethyl-8-nonen-3-one

생성물 1

HCID 59922918(5R,6S)-3-oxo-5-(2,2,2-trichloroethoxycarbonyl-oxy)-2,2,6-trimethyl-8-nonenal

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

A mixture of (5R,6S)-1,1-diisopropoxy-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,6-trimethyl-8-nonen-3-one (4.3 g) and p-toluenesulfonic acid monohydrate (0.45 g) in 100 mL of 3:1 THF/water is heated at reflux for 7 hours. The mixture is cooled and poured into sat. aq. NaHCO3, then extracted with ethyl acetate. The extract is dried over Na2SO4, filtered, and evaporated. The product is purified by chromatography on SiO2.

후처리

  1. temperatureis heated
  2. temperatureat reflux for 7 hours
  3. temperatureThe mixture is cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe product is purified by chromatography on SiO2

출처 및 근거

ORD 기록
ord-ff0fec4095954dc18dfb60f298b58d96
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176235B2

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