Phosphorus oxide (P4O10) → Ethyl [2-methyl-4-({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetyl)phenoxy]acetate

HRID 460027ノート

反応式

HRID 460027 の反応式
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][C:16]1[N:17]=[C:18]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[S:19][C:20]=1[CH2:21][C:22]([OH:24])=O.[CH3:35][C:36]1[CH:48]=[CH:47][CH:46]=[CH:45][C:37]=1[O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].C(=O)(O)[O-].[Na+]>CS(O)(=O)=O.O>[CH3:35][C:36]1[CH:48]=[C:47]([C:22](=[O:24])[CH2:21][C:20]2[S:19][C:18]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[N:17][C:16]=2[CH3:15])[CH:46]=[CH:45][C:37]=1[O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]

参加物

7

反応物 4

HCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium BicarbonateHCID 3022879Ethyl 2-(2-methylphenoxy)acetateHCID 17972178[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid2 回

生成物 1

HCID 58824797Ethyl [2-methyl-4-({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetyl)phenoxy]acetate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6395Methanesulfonic Acid溶媒

反応条件

温度
60 °C

実験手順

A well stirred suspension of phosphorus pentoxide (0.92 g) in methane sulfonic acid (6.5 ml) under nitrogen was heated to 60° C. until a clear solution formed. The mixture was then allowed to cool to room temperature prior to addition of {4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetic acid (intermediate 14, 0.98 g) and ethyl (2-methylphenoxy)acetate (0.49 ml). The mixture was heated to 60° C. for 90 minutes, after cooling to room temperature the reaction mixture was poured onto iced water (100 ml) and the acidic suspension basified by cautious addition of solid sodium bicarbonate. The product was extracted into ethyl acetate and the combined organic extracts dried (magnesium sulfate) filtered and evaporated. Purification by flash column chromatography using ethyl acetate:cyclohexane (1:9) as eluent gave title compound as a pale yellow solid.

後処理

  1. customformed
  2. temperatureto cool to room temperature
  3. temperatureThe mixture was heated to 60° C. for 90 minutes
  4. temperatureafter cooling to room temperature the reaction mixture
  5. extractionThe product was extracted into ethyl acetate
  6. dry with materialthe combined organic extracts dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by flash column chromatography

出典と根拠

ORDレコード
ord-49e54eb66b014b139ea23b4c48bc5329
出典データセット
uspto-grants-2007_03
特許番号
US07196107B2

反応ノート

読み込み中…