1,2-Dimethoxyethane → (1S,5R,6R,7R)-7-Benzoyloxy-6-[(E)-(4RS) 4-methyl-3-oxonon-1-en-7-inyl]-2-oxabicyclo[3,3,0]octan-3-one

HRID 1612863ノート

反応式

HRID 1612863 の反応式
[H-].[Na+].[CH:3]([C@H:5]1[C@H:12]([O:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][C@H:10]2[C@@H:6]1[CH2:7][C:8](=[O:22])[O:9]2)=O.[CH2:23]([CH2:26][O:27]C)OC>>[O:27]=[C:26]([CH:11]([CH3:10])[CH2:12][CH2:5][C:6]#[C:7][CH3:8])/[CH:23]=[CH:3]/[C@H:5]1[C@H:12]([O:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][C@H:10]2[C@@H:6]1[CH2:7][C:8](=[O:22])[O:9]2

参加物

4

反応物 3

HCID 80711,2-Dimethoxyethane3 回HCID 24758Sodium hydrideHCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

生成物 1

HCID 18650099(1S,5R,6R,7R)-7-Benzoyloxy-6-[(E)-(4RS) 4-methyl-3-oxonon-1-en-7-inyl]-2-oxabicyclo[3,3,0]octan-3-one

実験手順

A solution of 7.56 g of dimethyl-2-oxo-3 -methyl-6-octynylphosphate in 60 ml of dimethoxyethane is to a suspension of 1.33 g of sodium hydride (55% strength in oil) in 65 ml of dimethoxyethane at room temperature. Then the solution is agitated for 30 minutes at room temperature and cooled to -30° C. Subsequently, at -20° C., a solution of 7.66 g of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one in 84 ml of dimethoxyethane is added thereto and the mixture is stirred for another 2 hours at room temperature. The crude product is isolated analogously to Example (1a), thus obtaining 12.95 g of the title compound as an oil.

後処理

  1. temperaturecooled to -30° C
  2. stirringthe mixture is stirred for another 2 hours at room temperature
  3. customThe crude product is isolated analogously to Example (1a)

出典と根拠

ORDレコード
ord-c550614941054f4292084da1f46d88cf
出典データセット
uspto-grants-1993_03
特許番号
US05190973

反応ノート

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