Ethyl 2-(4,4,5,5,5-pentafluoropentyl)-9-decenoate → Ethyl 11-[17beta-hydroxy-3-methoxyestra-1,3,5(10)-trien-7alpha-yl]-2-(4,4,5,5,5-pentafluoropentyl)-9-undecenoate

HRID 460468ノート

反応式

HRID 460468 の反応式
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][CH2:10]4)[C@H:7]([CH2:22][CH:23]=[CH2:24])[CH2:6][C:5]=2[CH:4]=1.[F:25][C:26]([F:48])([C:44]([F:47])([F:46])[F:45])[CH2:27][CH2:28][CH2:29][CH:30]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]C=C)[C:31]([O:33][CH2:34][CH3:35])=[O:32]>ClCCl.C(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)C1C=CC=CC=1.Cl[Ru]Cl>[OH:21][C@H:12]1[CH2:11][CH2:10][C@H:9]2[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]12[CH3:14])[C:18]1[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:6][C@H:7]3[CH2:22][CH:23]=[CH:24][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH:30]([CH2:29][CH2:28][CH2:27][C:26]([F:25])([F:48])[C:44]([F:45])([F:46])[F:47])[C:31]([O:33][CH2:34][CH3:35])=[O:32]

参加物

5

反応物 2

HCID 12043786Ethyl 2-(4,4,5,5,5-pentafluoropentyl)-9-decenoateHCID 694148073-Methoxy-7alpha-(2-propenyl)estra-1,3,5(10)-trien-17beta-ol

生成物 1

HCID 86588527Ethyl 11-[17beta-hydroxy-3-methoxyestra-1,3,5(10)-trien-7alpha-yl]-2-(4,4,5,5,5-pentafluoropentyl)-9-undecenoate収率 67%

試薬・触媒・溶媒 2

HCID 90332616Dichlororuthenium;tricyclohexyl-[phenyl-(tricyclohexyl-lambda5-phosphanyl)methyl]-lambda5-phosphane触媒HCID 6344Dichloromethane溶媒

実験手順

Benzylidenebis(tricyclohexyl-phosphine)-dichlororuthenium (98 mg, 0.11 mmol) was added to a solution of 3-methoxy-7α-(2-propenyl)estra-1,3,5(10)-trien-17β-ol (723 mg, 2.21 mmol) and ethyl 2-(4,4,5,5,5-pentafluoropentyl)-9-decenoate (1.59 g, 4.43 mmol) in dichloromethane (20 ml), followed by heating under reflux for 20 hours under argon atmosphere. After cooling, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel flash chromatography (eluent: hexane/ethyl acetate=4/1) to give ethyl 11-[17β-hydroxy-3-methoxyestra-1,3,5(10)-trien-7α-yl]-2-(4,4,5,5,5-penta-fluoropentyl)-9-undecenoate (973 mg, Yield 67%).

後処理

  1. temperatureby heating
  2. temperatureunder reflux for 20 hours under argon atmosphere
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel flash chromatography (eluent: hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-25eebfeab96e4359a5828f2bf31e4b68
出典データセット
uspto-grants-2007_03
特許番号
US07196081B2

反応ノート

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