Ethanol → [2-(3-Methoxy-phenyl)-cyclohexyl]-acetic acid ethyl ester

HRID 418893

反応式

HRID 418893 の反応式
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH3:2].C(O)C>[Pd].O1CCCC1>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH3:2]

参加物

5

反応物 2

HCID 702EthanolHCID 193584881-(3-Methoxyphenyl)-2-(ethoxycarbonylmethyl)cyclohexene

生成物 1

HCID 66651961[2-(3-Methoxy-phenyl)-cyclohexyl]-acetic acid ethyl ester収率 89.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Combine [2-(3-methoxy-phenyl)-cyclohex-1-enyl]-acetic acid ethyl ester (9.91 g, 36.0 mmol), 10% Pd on carbon (2.06 g, 14.4 mmol), and ethanol (90 mL) and tetrahydrofuran (5 mL), degas, and add 50 psi H2 at room temperature. After 18 hours, filter off the Pd catalyst over celite eluting with ethyl acetate. Concentrate and flash chromatograph with 0% to 20% ethyl acetate/hexanes to yield the titled compound (8.89 g, 89%) as a clear oil. TLC Rf=0.42 in 6:1 hexanes:ethyl acetate. 1H NMR (CDCl3):1H NMR (CDCl3): 7.21 (t, 1H, J=8.1 Hz), 6.78 (d, 2H, J=7.5 Hz), 6.72 (s, 1H), 3.98 (q, 2H, J=7.0 Hz), 3.80 (m, 3H), 2.89 (m, 1H), 2.51 (m, 1H), 2.31 (m, 1H), 1.97 (m, 1H), 1.88 (m, 1H), 1.72 (m, 4H), 1.44 (m, 3H), 1.16 (t, 3H, J=6.6 Hz).

後処理

  1. additionadd 50 psi H2 at room temperature
  2. filtrationfilter off the Pd catalyst over celite
  3. washeluting with ethyl acetate
  4. concentrationConcentrate

出典と根拠

ORDレコード
ord-91d9d590bfe84817ae42a4e90d6f605f
出典データセット
uspto-grants-2012_01
特許番号
US08093302B2

関連ノート

読み込み中…