Diethyl Ether → HCID 66842955、化合物

HRID 2252360ノート

反応式

HRID 2252360 の反応式
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

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 10176127Pyridinium chlorideHCID 69099776HCID 69099776、化合物

生成物 1

HCID 66842955HCID 66842955、化合物収率 95.9%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
200 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c61985155cb64329ab2eb5091e3049d0
出典データセット
uspto-grants-2008_01
特許番号
US07321050B2

反応ノート

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