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Hydrochloric Acid → 5,5-dimethyl-4H,5H,6H-cyclopenta[b]thiophene-2-carboxylic acid

HRID 1021603
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HRID 1021603 반응식
[CH3:1][C:2]1([CH3:15])[CH2:14][C:5]2[S:6][C:7]([C:9]([O:11]CC)=[O:10])=[CH:8][C:4]=2[CH2:3]1.C1COCC1.[OH-].[Li+].Cl>C(O)C.O>[CH3:1][C:2]1([CH3:15])[CH2:14][C:5]2[S:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:4]=2[CH2:3]1
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58043720Ethyl 5,5-Dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate

생성물 1

HCID 580439285,5-dimethyl-4H,5H,6H-cyclopenta[b]thiophene-2-carboxylic acid수율 91%

시약·촉매·용매 2

HCID 702
Ethanol
용매
HCID 962Water용매

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온도
60 °C

실험 절차

In a 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser, 106b (4.00 g, 17.8 mmol) was dissolved in ethanol (50 mL). THF (50 mL), water (50 mL) and lithium hydroxide (854 mg, 35.6 mmol) were added, and the mixture was stirred at 60° C. for 4 h. After this time the reaction was cooled to room temperature and acidified with 2M hydrochloric acid to pH 1.5, and then extracted with ethyl acetate (2×200 mL). The organic layers were combined, washed with water (2×100 mL), followed by brine (100 ml) and dried over sodium sulfate. The drying agent was then separated by filtration. After evaporating the resulting filtrate, 106c was obtained in 91% yield (3.2 g) as a white solid: mp 170-172° C.; 1H NMR (300 MHz, CDCl3) δ 12.77 (s, 1H), 7.46 (s, 1H), 2.71 (s, 2H), 2.53 (s, 2H), 1.20 (s, 6H); MS (ESI−) m/z 195.0

후처리

  1. customIn a 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureAfter this time the reaction was cooled to room temperature
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. washwashed with water (2×100 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe drying agent was then separated by filtration
  8. customAfter evaporating the resulting filtrate

출처 및 근거

ORD 기록
ord-37279b153eae43478b5b60e97ad25608
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08716274B2

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