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

HRID 462790ノート

反応式

HRID 462790 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-46eb007713c84f9191cd2eb020126bd5
出典データセット
uspto-grants-1985_05
特許番号
US04517202

反応ノート

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