Sodium Bicarbonate → 5,12-Naphthacenedione, 1,2,3,4-tetrahydro-

HRID 234247

반응식

HRID 234247 반응식
[CH2:1]1[C:18]2[CH:5]([CH2:6][CH:7]3[CH:16]([CH:17]=2)[C:15](=[O:19])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]3)[CH2:4][CH2:3][CH2:2]1.C([O-])(O)=[O:21].[Na+].[N+]([O-])([O-])=O.[NH4+].[Ce]>CC(C)=O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>[CH2:13]1[C:14]2[C:15](=[O:19])[C:16]3[C:7](=[CH:6][C:5]4[C:18]([CH:17]=3)=[CH:1][CH:2]=[CH:3][CH:4]=4)[C:8](=[O:21])[C:9]=2[CH2:10][CH2:11][CH2:12]1

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 57418452Ammonium cerium-nitrateHCID 67719023Octahydro-11-naphthacenone

생성물 1

HCID 6214835,12-Naphthacenedione, 1,2,3,4-tetrahydro-수율 147.4%

시약·촉매·용매 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone촉매HCID 180Acetone용매2회

실험 절차

A solution of 36 mg (0.075 mmol) of the octahydro-11-naphthacenone and 60 mg (0.675 mmol) of NaHCO3 in 10 mL of acetone was treated with a solution of 167 mg (3 mmol) of cerium ammonium nitrate (CAN) and 1 mg of dichlorodicyanobenzoquinone (DDQ) in 2 mL of acetone added in one portion at 0 degrees centigrade. The reaction mixture was stirred at room temperature for 1.5 hours during which the color changed from shiny yellow to orange red, and then 25 mL of CH2Cl2 was added. The mixture was filtered through over Celite. The organic layer was washed with saturated NaCl solution (2×20 mL), dried over Na2SO4, and evaporated to give the tetrahydro-5,12-naphthacenedione as a red crystals (29 mg, 86 percent). mp greater than 258 degrees centigrade (decomp).

후처리

  1. additionadded in one portion at 0 degrees centigrade
  2. additionwas added
  3. filtrationThe mixture was filtered through over Celite
  4. washThe organic layer was washed with saturated NaCl solution (2×20 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated

출처 및 근거

ORD 기록
ord-f13e9e299b6c42f3a7fac25c2d29c638
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594158

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