Diethyl Ether → HCID 66842955, 화합물

HRID 2252360노트

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HRID 2252360 반응식
C[O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[CH:6]=[C:7]([O:12]C)[C:8]=1[CH:9]([CH3:11])[CH3:10].Cl.N1C=CC=CC=1.CCOCC>C(OCC)(=O)C>[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH:15]=[CH:14][C:5]1[CH:6]=[C:7]([OH:12])[C:8]([CH:9]([CH3:10])[CH3:11])=[C:3]([OH:2])[CH:4]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 10176127Pyridinium chlorideHCID 69099776HCID 69099776, 화합물

생성물 1

HCID 66842955HCID 66842955, 화합물수율 95.9%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
200 °C

실험 절차

A mixture of 2-(3,5-dimethoxy-4-i-propylphenyl)-1-(2-fluorophenyl)ethene (27B) (0.308 g, 1.03 mmol) and pyridine hydrochloride (0.72 g, 6.2 mmol) was heated at 200° C. for 4 h under a stream of argon. The reaction mixture was cooled to room temperature. 2NHCl (10 mL) and ether (15 mL) was added. The organic layer was separated and the aqueous layer was extracted with ether (3×10 mL). The extract was dried over anhydrous Na2SO4. Evaporation of ether followed by flash chromatography using 15% ethyl acetate in hexane afforded pure 5-[2-(2-fluorophenyl)ethenyl]-2-i-propyl-1,3-benzenediol (37B) (0.269 g, 95% yield) as an off-white solid. 1HNMR (CDCl3, ppm): δ 1.41 (d, J=7.2 Hz, 6H), 3.51 (qint., J=7.2 Hz, 1H), 5.01 (b, 2H), 6.56 (s, 2H), 6.98 (d, J=17.6 Hz, 1H), 7.0-7.3 (m, 4H), 7.60 (ddd, J=7.5, 7.5, 2.2 Hz, 1H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ether (3×10 mL)
  4. dry with materialThe extract was dried over anhydrous Na2SO4
  5. customEvaporation of ether

출처 및 근거

ORD 기록
ord-c61985155cb64329ab2eb5091e3049d0
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07321050B2

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