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Potassium Carbonate → Ethyl 7-hydroxy-2-methyl-1-benzothiophene-5-carboxylate

HRID 1643777
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HRID 1643777 반응식
C([O:4][C:5]1[C:13]2[S:12][C:11]([CH3:14])=[CH:10][C:9]=2[CH:8]=[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C.ClCCl>[OH:4][C:5]1[C:13]2[S:12][C:11]([CH3:14])=[CH:10][C:9]=2[CH:8]=[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=1
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참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 59560166Ethyl 7-(Acetyloxy)-2-methyl-1-benzothiophene-5-carboxylate

생성물 1

HCID 59560351Ethyl 7-hydroxy-2-methyl-1-benzothiophene-5-carboxylate수율 84%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매

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온도
60 °C

실험 절차

Ethyl 7-(acetyloxy)-2-methyl-1-benzothiophene-5-carboxylate was dissolved in absolute ethanol (500 mL). Potassium carbonate (18 g, 0.13 mol) was added. The reaction mixture was stirred for 3 h at 60° C. and diluted with 200 mL of dichloromethane. The suspension was filtered. The precipitate was washed by 100 mL of dichloromethane. The combined solutions were washed by 200 mL of a 10% aqueous solution of citric acid and evaporated in vacuum to dryness. The residue was crystallized from ether/hexane mixture (1:5) to give the desired product 10 g (42 mmol, 84%) as a cream solid. 1H NMR (DMSO-d6): δ ppm 1.30 (t, 3H), 2.50 (s, 3H), 4.30 (qt, 2H), 7.20 (s, 1H), 7.95(s, 1H), 7.85 (s, 1H); MS(APCl, pos): 237.1.

후처리

  1. filtrationThe suspension was filtered
  2. washThe precipitate was washed by 100 mL of dichloromethane
  3. washThe combined solutions were washed by 200 mL of a 10% aqueous solution of citric acid
  4. customevaporated in vacuum to dryness
  5. customThe residue was crystallized from ether/hexane mixture (1:5)

출처 및 근거

ORD 기록
ord-68adeafbf0ad42a788403b1b6249bf58
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08119624B2

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