Heptane → 7-bromo-3,4-dihydro-2H-1-benzopyran-4-one

HRID 1751402ノート

反応式

HRID 1751402 の反応式
[H-].C([Al+]CC(C)C)C(C)C.CCCCCCC.[Br:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23](=[O:29])[CH:24]=[CH:25][O:26]2)=[CH:21][CH:20]=1>O1CCCC1>[Br:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23](=[O:29])[CH2:24][CH2:25][O:26]2)=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 8900HeptaneHCID 186867527-BromochromoneHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 223357367-bromo-3,4-dihydro-2H-1-benzopyran-4-one収率 78.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of diisobutylaluminum hydride in heptane (1.0 M, 60 mL, 60.0 mmol) was added dropwise to a solution of 7-bromo-4H-chromen-4-one (4.5 g, 20.0 mmol) in tetrahydrofuran at −78° C. under an atmosphere of argon over a period of 30 minutes. After 30 minutes the reaction was quenched with a mixture of silica gel (10 g), and water (10 mL). The mixture was allowed to warm to room temperature and was filter through celite and the tetrahydrofuran was removed under reduced pressure. The residue was taken up in chloroform (100 mL) and washed with sodium hydroxide (1N, 25 mL) and dried over sodium sulfate. The mixture was filtered and the solvent was removed under reduced pressure. The residue was subjected to flash chromatography with eluant of dichloromethane. The product containing fractions were combined and the solvent was removed under reduced pressure to provide 7-bromochroman-4-one (3.57 g, 15.7 mmol, 78%).

後処理

  1. customAfter 30 minutes the reaction was quenched with a mixture of silica gel (10 g), and water (10 mL)
  2. filtrationwas filter through celite
  3. customthe tetrahydrofuran was removed under reduced pressure
  4. washwashed with sodium hydroxide (1N, 25 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationThe mixture was filtered
  7. customthe solvent was removed under reduced pressure
  8. additionThe product containing fractions
  9. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-2e62a9abe9414b9baf9a2f74f020e7b8
出典データセット
uspto-grants-2015_10
特許番号
US09156823B2

反応ノート

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