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

HRID 1173798

반응식

HRID 1173798 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-91effea2306a48d79f15731f4d9ceef7
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834054B2

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