Sodium Hydroxide → 3-(4-Bromo-5-methyl-thiophen-2-yl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole

HRID 68567

反応式

HRID 68567 の反応式
Cl.[NH2:2][OH:3].[OH-].[Na+].[Br:6][C:7]1[CH:8]=[C:9]([C:13](=O)[CH:14]=[C:15]([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)[C:16]([F:19])([F:18])[F:17])[S:10][C:11]=1[CH3:12]>CCO>[Br:6][C:7]1[CH:8]=[C:9]([C:13]2[CH2:14][C:15]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:3][N:2]=2)[S:10][C:11]=1[CH3:12]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 867066471-(4-Bromo-5-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-but-2-en-1-one

生成物 1

HCID 867066483-(4-Bromo-5-methyl-thiophen-2-yl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole収率 54.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Hydroxylamine hydrochloride (13 g) and NaOH (18 g) are added to a solution of 1-(4-bromo-5-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-but-2-en-1-one (84 g, 71% purity) in EtOH (1000 ml) at room temperature. After 12 hours at room, the reaction mixture is concentrated in vacuo, diluted with diethylether and water. The aqueous phase is separated and further extracted two times with diethylether. The organic phases are combined, washed with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is purified by chromatography on silica gel (1800 g) eluting with a mixture of heptane and dichloromethane (4:1) to yield 3-(4-bromo-5-methyl-thiophen-2-yl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (47 g) as a light brown crystals.

後処理

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. additiondiluted with diethylether and water
  3. customThe aqueous phase is separated
  4. extractionfurther extracted two times with diethylether
  5. washwashed with a saturated aqueous solution of NaCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by chromatography on silica gel (1800 g)
  9. washeluting with a mixture of heptane and dichloromethane (4:1)

出典と根拠

ORDレコード
ord-66a2043a24c04fb2af37d9d8c8b07f9a
出典データセット
uspto-grants-2014_09
特許番号
US08822466B2

関連ノート

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