2-Chloro-5-phenyl-thiophene-3-carboxylic acid ethyl ester → 2-Chloro-5-phenylthiophene-3-carboxylic acid

HRID 1914537ノート

反応式

HRID 1914537 の反応式
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:8][C:7]=1[Cl:17])=[O:5])C>[OH-].[Na+].C(O)C>[Cl:17][C:7]1[S:8][C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:10][C:6]=1[C:4]([OH:5])=[O:3]

参加物

4

反応物 1

HCID 581102772-Chloro-5-phenyl-thiophene-3-carboxylic acid ethyl ester

生成物 1

HCID 581102042-Chloro-5-phenylthiophene-3-carboxylic acid収率 43.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
100 °C

実験手順

2-Chloro-5-phenyl-thiophene-3-carboxylic acid ethyl ester (0.44 g, 1.65 mmol) was dissolved in a solution of 1 M NaOH (3 mL) and ethanol (2 mL). The reaction mixture was heated to 100° C. using microwave irradiation for 10 minutes. After cooling, the reaction mixture was partitioned between diethyl ether and water. The aqueous solution was acidified with 1 M HCl and further extracted with diethyl ether. The combined organic solutions were dried over magnesium sulfate, filtered and the solvent evaporated. The residue was triturated in diethyl ether and filtered to give the title compound (0.17 g). 1H NMR (400 MHz, CHCl3-d): δ 7.6 (s, 1H), 7.55 (d, 2H), 7.4-7.3 (m, 3H).

後処理

  1. custommicrowave irradiation for 10 minutes
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between diethyl ether and water
  4. extractionfurther extracted with diethyl ether
  5. dry with materialThe combined organic solutions were dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was triturated in diethyl ether
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-d065559b7a884d1db642ceaa38a97027
出典データセット
uspto-grants-2013_12
特許番号
US08614209B2

反応ノート

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