Sulfuric Acid → 10-Cycloeicosenone

HRID 1883289

반응식

HRID 1883289 반응식
[OH:1][CH:2]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.C1(C)C=CC=CC=1.S(=O)(=O)(O)O>[Zn].O>[C:2]1(=[O:1])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 1140Toluene2회HCID 673128522-Hydroxy-11-cycloeicosenone

생성물 1

HCID 6731346910-Cycloeicosenone수율 92%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

In a 50 ml four neck reactor equipped with a thermometer, a dripping funnel and a refrigerant, zinc powder (2.3 g), 2-hydroxy-11-cycloeicosenone (1.4 g) and toluene (10 ml) were mixed, stirred and heated at 90° C. under a nitrogen flow. A 20N sulphuric acid aqueous solution (2.8 ml) was added thereto dropwise over 2.5 hours, and the resulting mixture was stirred under heating for 30 minutes. After the reaction, the mixture was supplemented with toluene and water, and allowed to stand to separate into two phases. The organic phase thus obtained was washed twice with water and then with a saturated sodium chloride aqueous solution. The solvent was removed under reduced pressure to give 1.4 g of crude product. This latter was purified on a silica gel column chromatography (hexane/ethyl acetate=10/1, v/v) to give 1.2 g of 10-cycloeicosenone (yield 92%).

후처리

  1. stirringthe resulting mixture was stirred
  2. temperatureunder heating for 30 minutes
  3. customAfter the reaction
  4. customto separate into two phases
  5. customThe organic phase thus obtained
  6. washwas washed twice with water
  7. customThe solvent was removed under reduced pressure
  8. customto give 1.4 g of crude product
  9. customThis latter was purified on a silica gel column chromatography (hexane/ethyl acetate=10/1

출처 및 근거

ORD 기록
ord-a68d66c72050437faeaba63c2ae9b3ae
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759557B2

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