Acetic Acid → 6-bromo-2,2-dimethyl-3-methylene-2,3-dihydro-4H-chromen-4-one

HRID 594881

反応式

HRID 594881 の反応式
CN(C)CN(C)C.[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]2=[O:21].[C:22](O)(=O)C.C(OC(=O)C)(=O)C>O1CCCC1>[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:19])([CH3:20])[C:13](=[CH2:22])[C:12]2=[O:21]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7918Acetic AnhydrideHCID 147553646-bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

生成物 1

HCID 867242786-bromo-2,2-dimethyl-3-methylene-2,3-dihydro-4H-chromen-4-one収率 87.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

N,N,N′,N′-tetramethylmethanediamine (4.8 g, 47 mmol) was added to a solution of 6-bromo-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (3.0 g, 12 mmol) and acetic acid (0.67 ml, 12 mmol) in tetrahydrofuran (43 ml), and the mixture was stirred at 70° C. for 24 hours. To the mixture was added acetic anhydride (4.4 ml, 47 mmol), and the mixture was stirred at 70° C. for 4 hours and concentrated in vacuo. The residue was directly purified by silica gel column chromatography (hexane/ethyl acetate=20:1) to afford 6-bromo-2,2-dimethyl-3-methylene-2,3-dihydro-4H-chromen-4-one (2.8 g).

後処理

  1. stirringthe mixture was stirred at 70° C. for 4 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was directly purified by silica gel column chromatography (hexane/ethyl acetate=20:1)

出典と根拠

ORDレコード
ord-3d64f1bf0ce24835970266559e585534
出典データセット
uspto-grants-2016_01
特許番号
US09242973B2

関連ノート

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