Tetrahydrofuran → 4-(chloromethyl)-5-(5-chlorothiophen-2-yl)isoxazole

HRID 1794332ノート

反応式

HRID 1794332 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH2:12]O)=[CH:4][CH:3]=1.O1CCCC1.S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:21][CH2:12][C:8]1[CH:9]=[N:10][O:11][C:7]=1[C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 22221030HCID 22221030、化合物

生成物 1

HCID 222213324-(chloromethyl)-5-(5-chlorothiophen-2-yl)isoxazole収率 98.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a mixture of 5-(5-chloro-2-thienyl)-4-isoxazolylmethanol (6.54 g), tetrahydrofuran (20 ml) and toluene (100 ml) was added dropwise thionyl chloride (5.41 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, saturated aqueous sodium hydrogencarbonate was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and crystals of 4-chloromethyl-5-(5-chloro-2-thienyl)isoxazole (6.98 g, yield 98%) were obtained from a fraction eluted with ethyl acetate-hexane (1:5, volume ratio) and recrystallized from ethyl acetate-hexane to give a colorless prism. melting point: 70–71° C.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionsaturated aqueous sodium hydrogencarbonate was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-6994acdbd83745d39055188979b8b893
出典データセット
uspto-grants-2006_04
特許番号
US07022725B2

反応ノート

読み込み中…