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Ethyl 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylate → 5-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylic acid

HRID 1188885
ノート
印刷プレビュー

反応式

HRID 1188885 の反応式
[CH3:1][S:2]([C:5]1[CH:33]=[CH:32][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([O:19][CH2:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:18]=2)[NH:15][C:14]([C:27]([O:29]CC)=[O:28])=[CH:13]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>O1CCCC1.C(O)C.[OH-].[Na+]>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([O:19][CH2:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:18]=2)[NH:15][C:14]([C:27]([OH:29])=[O:28])=[CH:13]3)=[CH:32][CH:33]=1)(=[O:3])=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 66898356Ethyl 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylate

生成物 1

HCID 668978135-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylic acid収率 33.4%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide
溶媒

反応条件

温度
50 °C

実験手順

Ethyl 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylate (3.5 g) was dissolved in a mixed solvent of tetrahydrofuran (30 mL)-ethanol (30 mL), 1M aqueous sodium hydroxide solution (15 mL) was added, and the mixture was stirred at 50° C. for 1 hr. The reaction solution was allowed to cool to room temperature, and concentrated under reduced pressure. Water was added to the residue, and the mixture was neutralized with 1M hydrochloric acid, and subjected to extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained crude product was crystallized from a mixed solvent of ethanol-hexane-diethyl ether. The obtained colorless crystals were recrystallized from acetone-hexane to give the title compound (1.1 g) as colorless crystals. melting point 256-258° C. (decomposition).

後処理

  1. additionwas added
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionsubjected to extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained crude product
  11. customwas crystallized from a mixed solvent of ethanol-hexane-diethyl ether
  12. customThe obtained colorless crystals were recrystallized from acetone-hexane

出典と根拠

ORDレコード
ord-ee20c4cbabf942a2bb9b31cf19e34e06
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08673942B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート