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

HRID 2296866ノート

反応式

HRID 2296866 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-988365bd04604c24894956a009cba339
出典データセット
uspto-grants-2002_12
特許番号
US06489314B1

反応ノート

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