Sulfuric Acid → methyl 2,3-dihydrobenzofuran-5-carboxylate

HRID 2181645노트

반응식

HRID 2181645 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.S(=O)(=O)(O)O.[C:18](=O)(O)[O-].[Na+]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:18])=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 6765832,3-Dihydrobenzo(b)furan-5-carboxylic acid

생성물 1

HCID 2821720methyl 2,3-dihydrobenzofuran-5-carboxylate수율 98%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 2,3-dihydrobenzofuran-5-carboxylic acid (3.96 g, 24.1 mmol) in MeOH (200 mL) is added concentrated sulfuric acid (0.5 mL). The mixture is heated to reflux for 24 h. The mixture is cooled to rt, followed by the addition of solid sodium bicarbonate. The reaction mixture is concentrated in vacuo, and the remaining residue is partitioned between EtOAc and water. The aqueous layer is extracted with EtOAc, and the combined organic layers are dried (MgSO4), filtered and concentrated in vacuo to afford 4.22 g (98%) of methyl 2,3-dihydrobenzofuran-5-carboxylate as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.93-7.89, 6.82, 4.69, 3.86, 3.28.

후처리

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 24 h
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customthe remaining residue is partitioned between EtOAc and water
  5. extractionThe aqueous layer is extracted with EtOAc
  6. dry with materialthe combined organic layers are dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-64f4b7366b3a4f8abbb92aa72e26373d
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894042B2

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