Stearic Acid → Methyl 3-oxoicosanoate

HRID 888748

반응식

HRID 888748 반응식
[C:1](O)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]C.C[C:22]1(C)[O:27][C:26](=[O:28])[CH2:25][C:24](=[O:29])O1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>C(Cl)Cl>[O:29]=[C:24]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:25][C:26]([O:27][CH3:22])=[O:28]

참가 물질

6

반응물 4

HCID 5281Stearic AcidHCID 8471TriethylamineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 76257Diethyl cyanophosphonate

생성물 1

HCID 84502Methyl 3-oxoicosanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Stearic acid (5.0 g, 17.6 mmoles) is suspended in methylene chloride (88 mL) and 2,2-dimethyl-1,3-dioxane-4,6-dione (2.7 g, 18.5 mmoles), triethylamine (6.7 mL, 48.0 mmoles) and diethyl cyanophosphonate (2.7 mL, 17.6 mmoles) are added. All solids dissolve quickly. The solution is stirred for 16 hours at ambient temperature. The reaction mixture is then diluted with methylene chloride (100 mL) and carefully washed three times with aqueous hydrochloric acid (3 M, 50 mL each), three times with water (50 mL each) and once with saturated aqueous sodium chloride (50 mL). The reaction mixture is then dried over anhydrous sodium sulfate, filtered and evaporated. The resulting syrup is dissolved in anhydrous methanol (100 mL) and heated to reflux for 16 hours. The methanol is evaporated and the crude product dissolved in hexanes with slight heating. The crude product was then loaded on silica gel (150 mL bed volume) eluting with hexanes (500 mL) then hexane:acetone (98:2 [v/v], 1000 mL). Fractions containing pure product by thin layer chromatography are pooled and evaporated to dryness. The resulting oil is dried well in vacuo. The yield is 5.2 g (87%).

후처리

  1. dissolutionAll solids dissolve quickly
  2. washcarefully washed three times with aqueous hydrochloric acid (3 M, 50 mL each), three times with water (50 mL each)
  3. dry with materialThe reaction mixture is then dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe resulting syrup is dissolved in anhydrous methanol (100 mL)
  7. temperatureheated
  8. temperatureto reflux for 16 hours
  9. customThe methanol is evaporated
  10. dissolutionthe crude product dissolved in hexanes with slight heating
  11. washeluting with hexanes (500 mL)
  12. additionFractions containing pure product by thin layer chromatography
  13. customevaporated to dryness
  14. customThe resulting oil is dried well in vacuo

출처 및 근거

ORD 기록
ord-02b8d72175974ef1a07f755ec44e8453
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252755B2

연결된 노트

불러오는 중…