Cyclododecanone → 1-Oxaspiro[2.11]tetradecane

HRID 37303

반응식

HRID 37303 반응식
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]1(=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>O>[O:21]1[C:9]2([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:4]1

참가 물질

5

반응물 3

HCID 13246CyclododecanoneHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

생성물 1

HCID 110198001-Oxaspiro[2.11]tetradecane수율 78.7%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a dry flask under nitrogen is added 3.1 g (64.6 mmol) of 50% sodium hydride in mineral oil. The sodium hydride is washed twice with hexanes, is suspended in 80 ml of dry dimethyl sulfoxide and then 14.3 g (65.0 mmol) of trimethylsulfoxonium iodide is added. The mixture is stirred at room temperature for several hours and then 11.8 g (64.7 mmol) of cyclododecanone is introduced. The mixture is allowed to stir overnight at room temperature and then is heated. for 1 hour at 50° C. The mixture is cooled to room temperature, is dissolved in 500 ml of cold water and is extracted seven times with ethyl ether. The combined organic layers are washed once with water, dried over magnesium sulfate and subjected to evaporation in vacuo. The residue is chromatographed on silica gel using 20% ethyl acetate/hexanes as the mobile phase to give 10 g (78%) of the title compound as a colorless oil: NMR (CDCl3) δ 1.2-1.8 (m, 18 H), 2.05 (s, 1H), 2.4 (t, 2H, J=5.0 Hz), 2.45 (d, 2H), 2.58 (s, 2H ).

후처리

  1. washThe sodium hydride is washed twice with hexanes
  2. stirringto stir overnight at room temperature
  3. temperatureis heated
  4. temperatureThe mixture is cooled to room temperature
  5. extractionis extracted seven times with ethyl ether
  6. washThe combined organic layers are washed once with water
  7. dry with materialdried over magnesium sulfate
  8. customsubjected to evaporation in vacuo
  9. customThe residue is chromatographed on silica gel using 20% ethyl acetate/hexanes as the mobile phase

출처 및 근거

ORD 기록
ord-0cc29cc29f4c4d50ba5474fb0a790392
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420153

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