Epichlorohydrin → 3-(3,5-Dimethyl-4-oxiranylmethoxy-phenyl)-5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazole

HRID 1094301ノート

反応式

HRID 1094301 の反応式
[CH2:1]([C:3]1[S:7][C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[C:17]([CH3:19])[C:16]([OH:20])=[C:15]([CH3:21])[CH:14]=3)[N:9]=2)=[CH:5][CH:4]=1)[CH3:2].[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>C(O)(C)C.[OH-].[Na+].C(OCC)C>[CH3:21][C:15]1[CH:14]=[C:13]([C:10]2[N:9]=[C:8]([C:6]3[S:7][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=3)[O:12][N:11]=2)[CH:18]=[C:17]([CH3:19])[C:16]=1[O:20][CH2:22][CH:24]1[CH2:25][O:26]1

参加物

6

反応物 2

HCID 7835EpichlorohydrinHCID 1360299474-[5-(5-Ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol

生成物 1

HCID 866393493-(3,5-Dimethyl-4-oxiranylmethoxy-phenyl)-5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazole収率 28.3%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 3776Isopropanol溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
40 °C

実験手順

A mixture of 4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol (367 mg, 1.22 mmol) and epichlorohydrine (565 mg, 6.10 mmol) in isopropanol (20 mL) and 3 N aq. NaOH (6 mL) is stirred at 40° C. for 15 h. The mixture is diluted with diethyl ether, washed with sat. aq. NaHCO3 and water, dried over MgSO4, filtered and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazole (123 mg) as a pale yellow oil; LC-MS: tR=1.15 min, [M+1]+=357.11.

後処理

  1. washwashed with sat. aq. NaHCO3 and water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

出典と根拠

ORDレコード
ord-89196b5213394a1b88508c0ee932dcda
出典データセット
uspto-grants-2012_03
特許番号
US08133910B2

反応ノート

読み込み中…