Hydrochloric Acid → 5-(2-Pyrrolidin-1-ylethoxy)benzofuran-2-carboxylic acid

HRID 914269ノート

反応式

HRID 914269 の反応式
C[O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:10][C:8]=2[CH:9]=1)=[O:4].[OH-].[Li+].Cl>O1CCOCC1>[N:17]1([CH2:16][CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:7]3[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][C:8]=3[CH:10]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 666882085-(2-Pyrrolidin-1-ylethoxy)benzofuran-2-carboxylic acid methyl ester

生成物 1

HCID 229283195-(2-Pyrrolidin-1-ylethoxy)benzofuran-2-carboxylic acid収率 58.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To an ice-cooled solution of 5-(2-pyrrolidin-1-ylethoxy)benzofuran-2-carboxylic acid methyl ester (960 mg, 3.3 mmol) anhydrous ethylene glycol dimethyl ether (10 ml) was added dropwise degassed aqueous lithium hydroxide solution (2.0 ml, 2.0M). After stirring at room temperature for 4 h, the solution was cooled down and the pH was adjusted to 2 with 4.0 M HCl in dioxane. A gummy tan precipitate formed. The solvent was removed and the gummy residue was frozen and lyophilized. The tan colored solid was dissolved in boiling 2-propanol (90 ml), the solution was filtered hot and then cooled to give 5-(2-pyrrolidin-1-yl-ethoxy)-benzofuran-2-carboxylic acid as beige colored needles (528 mg). Additional 153 mg was obtained from the mother liquor.

後処理

  1. temperaturethe solution was cooled down
  2. customA gummy tan precipitate formed
  3. customThe solvent was removed
  4. temperaturethe gummy residue was frozen
  5. dissolutionThe tan colored solid was dissolved
  6. filtrationthe solution was filtered hot
  7. temperaturecooled

出典と根拠

ORDレコード
ord-ab17a41656d6415896ec9d21c4ccf38e
出典データセット
uspto-grants-2011_09
特許番号
US08026371B2

反応ノート

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