Catechol → Benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester

HRID 10616

反応式

HRID 10616 の反応式
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].Br[C:10](Br)([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:19]([O:18][C:16]([C:10]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1)=[O:17])[CH3:20]

参加物

5

反応物 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 69427Propanedioic acid, 2,2-dibromo-, 1,3-diethyl ester

生成物 1

HCID 12969876Benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester収率 73.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Ex-1A: Catechol (2.2 g, 20 mmol) was dissolved in acetone. Diethyl dibromomalonate (7.0 g, 22 mmol) and potassium carbonate (2.76 g) were added, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and water was added to the residue. The residue was extracted with dichloromethane, and the organic phase was washed with brine, dried over magnesium sulfate and evaporated. Chromatography (hexanes/ethyl acetate, 4:1) gave 3.9 g of benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester. 1H-NMR (CDCl3) δ 6.90–6.97 (m, 4H), 4.37 (q, J=7 Hz, 4H), 1.32 (t, J=7 Hz, 6H).

後処理

  1. customThe solvent was removed under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionThe residue was extracted with dichloromethane
  4. washthe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

出典と根拠

ORDレコード
ord-0fb2734542694c16affef6dddddfd246
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

関連ノート

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