Acetone → HCID 21541491、化合物

HRID 1076014ノート

反応式

HRID 1076014 の反応式
[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[C:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]1[CH:33]([C:34]#[N:35])[CH:32]([OH:36])[CH2:31][C:30]1=[O:37])([O:21][CH3:22])=[O:20].CC(C)=O.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>O1CCCC1>[C:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]1[CH:33]([C:34]#[N:35])[CH:32]([OH:36])[CH2:31][CH:30]1[OH:37])([O:21][CH3:22])=[O:20]

参加物

6

反応物 4

HCID 180AcetoneHCID 6097028Ammonium SulfateHCID 16710494Lithium tri-tert-butoxyaluminohydride2 回HCID 21541490HCID 21541490、化合物

生成物 1

HCID 21541491HCID 21541491、化合物収率 79.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Into a suspension of 8 g of lithium tri-t-butoxyaluminum hydride in 90 ml of absolute tetrahydrofuran was added dropwise 4.0 g of 2-(6'-carbomethoxyhexyl)-3-cyano-4-hydroxy-cyclopentanone under ice-cooling. The obtained mixture remained under ice-cooling for 1.5 hours and then at room temperature for 0.5 hours. After cooling, acetone and an aqueous solution saturated with ammonium sulfate were added to the reaction mixture to decompose the excess lithium tri-t-butoxyaluminum hydride and the complex salt product. The resultant oily layer was extracted with ethyl acetate, and the extract was washed with water, dried and then concentrated to afford 3.2 g of 2-(6'-carbomethoxyhexyl)-3-cyano-cyclopentane-1,4-diol as an oily substance, which was purified using chromatography on silica gel.

後処理

  1. temperaturecooling
  2. temperaturecooling for 1.5 hours
  3. temperatureAfter cooling
  4. extractionThe resultant oily layer was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. customdried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-b41e421a838a41028fb6c32d88c6dbe5
出典データセット
uspto-grants-1976_05
特許番号
US03954811

反応ノート

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