Dimethylformamide → 1a,7b-Dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carboxaldehyde

HRID 1030210ノート

反応式

HRID 1030210 の反応式
Br[C@H:2]1[C@H:7]([OH:8])[C:6]2[CH:9]=[C:10]([CH:13]=[O:14])[CH:11]=[CH:12][C:5]=2[O:4][C:3]1([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:15][C:3]1([CH3:16])[CH:2]2[O:8][CH:7]2[C:6]2[CH:9]=[C:10]([CH:13]=[O:14])[CH:11]=[CH:12][C:5]=2[O:4]1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 13704275HCID 13704275、化合物

生成物 1

HCID 137042811a,7b-Dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carboxaldehyde収率 58.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of trans-3-bromo-3,4-dihydro-2,2-dimethyl-4-hydroxy-2H-1-benzopyran-6-carbaldehyde (6.9 g), potassium carbonate (6.7 g), and dimethylformamide (24 ml) was stirred at room temperature for 48 hours and followed by at 35° C. for 24 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by recrystallization from diisopropyl ether to give 3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-1-benzopyran-6-carbaldehyde (2.9 g).

後処理

  1. waitfollowed by at 35° C. for 24 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by recrystallization from diisopropyl ether

出典と根拠

ORDレコード
ord-48fdf6e283364909b8404b22e04bef0a
出典データセット
uspto-grants-1992_04
特許番号
US05104890

反応ノート

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