Potassium Hydroxide → 2-Ethyl-4-[4-(methylsulfonyl)phenoxy]-1-benzofuran-6-carboxylic acid

HRID 1643738노트

반응식

HRID 1643738 반응식
[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14]CC)=[O:13])[CH:9]=[C:8]([O:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[C:6]=2[CH:7]=1)[CH3:2].[OH-].[K+]>CO.O>[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[C:8]([O:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[C:6]=2[CH:7]=1)[CH3:2]

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 59560127Ethyl 2-ethyl-4-[4-(methylsulfonyl)phenoxy]-1-benzofuran-6-carboxylate

생성물 1

HCID 595599412-Ethyl-4-[4-(methylsulfonyl)phenoxy]-1-benzofuran-6-carboxylic acid수율 94%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A mixture of ethyl 2-ethyl-4-[4-(methylsulfonyl)phenoxy]-1-benzofuran-6-carboxylate (0.80 g, 2.1 mmol) and KOH (0.35 g, 6.3 mmol) in MeOH (40 mL) and water (4 mL) was heated to reflux overnight. The reaction was monitored by TLC (petroleum ether/EtOAc 4:1). The reaction mixture was concentrated to dryness and poured into water (50 mL). The aqueous layer was acidified to pH˜2 with concentrated HCl (4 mL) and extracted with EtOAc (50 mL×3). The organic layer was washed with brine (50 mL×2), dried over Na2SO4 and concentrated to afford the desired compound (0.70 g, 94%) as an off-white solid.

후처리

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated to dryness
  4. additionpoured into water (50 mL)
  5. extractionextracted with EtOAc (50 mL×3)
  6. washThe organic layer was washed with brine (50 mL×2)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cf38b756870b45cca86ff6b3deec51f4
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119624B2

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