Water → 2-(3,4-Diethoxyphenyl)-4-styrylthiazole

HRID 1489251ノート

反応式

HRID 1489251 の反応式
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH2:6]([O:8][C:9]1[CH:10]=[C:11]([C:18]2[S:19][CH:20]=[C:21]([CH:23]=O)[N:22]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[CH3:7].O.C(OCC)(=O)C.O1C[CH2:35][CH2:34][CH2:33]1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>[CH2:6]([O:8][C:9]1[CH:10]=[C:11]([C:18]2[S:19][CH:20]=[C:21]([CH:23]=[CH:4][C:3]3[CH:35]=[CH:34][CH:33]=[CH:1][CH:2]=3)[N:22]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[CH3:7]

参加物

7

反応物 5

HCID 962WaterHCID 8028Tetrahydrofuran2 回HCID 8857Ethyl AcetateHCID 187072072-(3,4-Diethoxyphenyl)-4-formylthiazoleHCID 178418339Butyllithium

生成物 1

HCID 539918722-(3,4-Diethoxyphenyl)-4-styrylthiazole

試薬・触媒・溶媒 1

HCID 70671Benzyltriphenylphosphonium chloride触媒

反応条件

温度
-50 °C

実験手順

4.2 ml of n-butyllithium was dropwise added in small portions to a suspension of 2.6 g of benzyltriphenylphosphonium chloride in 10 ml of tetrahydrofuran, with stirring at -50° C. The mixture was heated to room temperature and, after cooling again to -50° C., was mixed with 12 ml of a tetrahydrofuran solution of 2 g of 2-(3,4-diethoxyphenyl)-4-formylthiazole. The mixture was stirred at the same temperature for 30 minutes and at room temperature for 14 hours. 10 ml of water and 40 ml of ethyl acetate were added to conduct extraction and phase separation. The solvent layer was dried and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography to obtain 2 g of 2-(3,4-diethoxyphenyl)-4-styrylthiazole as a 1:1 mixture of cis form and trans form.

後処理

  1. temperatureThe mixture was heated to room temperature
  2. temperatureafter cooling again to -50° C.
  3. stirringThe mixture was stirred at the same temperature for 30 minutes and at room temperature for 14 hours
  4. extractionextraction and phase separation
  5. customThe solvent layer was dried
  6. distillationsubjected to distillation
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b9784346ad6e4544bd81b6580dc32da1
出典データセット
uspto-grants-1997_10
特許番号
US05677319

反応ノート

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