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

HRID 1660297노트

반응식

HRID 1660297 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 130418335-Hydroxy-hexahydro-pentalen-2-one수율 77.3%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a903e17f43fe4c0a97a3f61c7791fb6d
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04307112

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