Endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-5,8-dione → 1,4,4a,5,8,8a-Hexahydro-1,4-ethanonaphthalene-5,8-diol

HRID 1879344

반응식

HRID 1879344 반응식
[CH:1]12[CH2:12][CH2:11][CH:8]([CH:9]=[CH:10]1)[CH:7]1[CH:2]2[C:3](=[O:14])[CH:4]=[CH:5][C:6]1=[O:13].[BH4-].[Na+]>CO>[CH:8]12[CH2:11][CH2:12][CH:1]([CH:10]=[CH:9]1)[CH:2]1[CH:7]2[CH:6]([OH:13])[CH:5]=[CH:4][CH:3]1[OH:14]

참가 물질

4

반응물 2

HCID 137731Endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-5,8-dioneHCID 4311764Sodium borohydride

생성물 1

HCID 126575751,4,4a,5,8,8a-Hexahydro-1,4-ethanonaphthalene-5,8-diol수율 106.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 25.6 g of tricyclo[6.2.2.02,7]dodeca-4,9-diene-3,6-dione in 600 mL of MeOH were added 58.0 g of CeCl3 7H2O. Then, 5.7 g of NaBH4 were portionwise added at 0° C. and the mixture was stirred for 1 h at the same temperature. After evaporation of the solvent the residue was redissolved in EtOAc, it was washed with H2O, dried over MgSO4 and concentrated in vacuo. The crude was again redissolved in EtOAc and triturated with Hept to obtain 27.9 g of the desired compound as mixture of stereoisomers as brownish solid.

후처리

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas redissolved in EtOAc
  3. washit was washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude was again redissolved in EtOAc
  7. customtriturated with Hept

출처 및 근거

ORD 기록
ord-f94c1a785c364590b5151d146b8595fd
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314253B2

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