Acetic Acid → (E)-6-acetoxy-2-(3-oxooct-1-enyl)bicyclo[3,3,0]octane

HRID 462790노트

반응식

HRID 462790 반응식
[Na].[O:2]=[C:3]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:4]P(=O)(OC)OC.[C:16]([O:19][CH:20]1[CH2:27][CH2:26][CH:25]2[CH:21]1[CH2:22][CH2:23][CH:24]2[CH:28]=O)(=[O:18])[CH3:17].C(O)(=O)C>O1CCCC1.C(OCC)C>[C:16]([O:19][CH:20]1[CH2:27][CH2:26][CH:25]2[CH:21]1[CH2:22][CH2:23][CH:24]2/[CH:28]=[CH:4]/[C:3](=[O:2])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=[O:18])[CH3:17]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 580181Dimethyl (2-oxoheptyl)phosphonateHCID 5360545SodiumHCID 203971916-Acetoxy-2-formylbicyclo[3,3,0]octane

생성물 1

HCID 20397216(E)-6-acetoxy-2-(3-oxooct-1-enyl)bicyclo[3,3,0]octane

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A suspension of the sodium salt of dimethyl (2-oxoheptyl)phosphonate (0.105 g; prepared as described in Reference Example 55) in tetrahydrofuran (5.3 ml) at 0° C. was treated dropwise with a solution of 6-acetoxy-2-formylbicyclo[3,3,0]octane (70 mg; prepared as described in Reference Example 21 and predominantly in the 2β-configuration) in tetrahydrofuran (1.0 ml) with stirring. The resulting mixture was stirred for 18 hours at ambient temperature under an atmosphere of argon. The mixture was then treated dropwise with a solution of glacial acetic acid (200 mg) in diethyl ether (1 ml), and then the solution was concentrated in vacuo. The residue was treated with diethyl ether (20 ml) and water (20 ml) and the organic layer was separated. The aqueous layer was extracted with diethyl ether (3×20 ml). The combined extracts were washed with water and then with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo, to give an oil which was subjected to chromatography on a silica gel column, to give (E)-6-acetoxy-2-(3-oxooct-1-enyl)bicyclo[3,3,0]octane (65.7 mg), predominantly in the 2β-configuration.

후처리

  1. customprepared
  2. concentrationthe solution was concentrated in vacuo
  3. additionThe residue was treated with diethyl ether (20 ml) and water (20 ml)
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with diethyl ether (3×20 ml)
  6. washThe combined extracts were washed with water
  7. dry with materialwith saturated aqueous sodium chloride solution, dried over magnesium sulphate
  8. concentrationconcentrated in vacuo
  9. customto give an oil which

출처 및 근거

ORD 기록
ord-46eb007713c84f9191cd2eb020126bd5
출처 데이터셋
uspto-grants-1985_05
특허 번호
US04517202

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