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

HRID 234247

反応式

HRID 234247 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone触媒HCID 180Acetone溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f13e9e299b6c42f3a7fac25c2d29c638
出典データセット
uspto-grants-1997_01
特許番号
US05594158

関連ノート

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