Acetic Acid → 5-Hydroxy-hexahydro-pentalen-2-one

HRID 1660297ノート

反応式

HRID 1660297 の反応式
[BH4-].[Na+].[CH:3]12[CH2:10][C:9](=[O:11])[CH2:8][CH:7]1[CH2:6][C:5](=[O:12])[CH2:4]2.CC(C)=O.C(O)(=O)C>C(Cl)Cl.C(O)C.O>[OH:12][CH:5]1[CH2:4][CH:3]2[CH:7]([CH2:8][C:9](=[O:11])[CH2:10]2)[CH2:6]1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 180AcetoneHCID 103526cis-Tetrahydropentalene-2,5(1H,3H)-dioneHCID 4311764Sodium borohydride

生成物 1

HCID 130418335-Hydroxy-hexahydro-pentalen-2-one収率 77.3%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

1.1 g of sodium borohydride (0.029 mol) is added with stirring to a solution of 11.6 g of bicyclo[3.3.0]octane-3,7-dione (8.4×10-2 mol) in 100 ml of methylene chloride and 100 ml of ethanol. After 45 minutes at this temperature, the excess reagent is decomposed by slowly adding 20 ml of acetone. The mixture is then neutralized with 1.4 ml of acetic acid, and evaporated under vacuum to afford a residue which is taken up in water and methylene chloride. The organic phase is evaporated to dryness and filtered on silica gel (70:30 hexane:ethyl ether as eluent) to afford 9.1 g of 7ξ-hydroxy-bicyclo[3.3.0]octan-3-one.

後処理

  1. customevaporated under vacuum
  2. customto afford a residue which
  3. customThe organic phase is evaporated to dryness
  4. filtrationfiltered on silica gel (70:30 hexane:ethyl ether as eluent)

出典と根拠

ORDレコード
ord-a903e17f43fe4c0a97a3f61c7791fb6d
出典データセット
uspto-grants-1981_12
特許番号
US04307112

反応ノート

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