Ethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-decenoate → Ethyl 11-[3,17beta-bis(benzyloxy)estra-1,3,5(10), 9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoate

HRID 1582826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582826
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][C:22]=3[CH2:27][CH:28]=[CH2:29])([CH3:20])[C@@H:18]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:38][C:39]([F:66])([C:56]([F:65])([F:64])[C:57]([F:63])([F:62])[C:58]([F:61])([F:60])[F:59])[CH2:40][CH2:41][CH:42]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]C=C)[C:43]([O:45][CH2:46][CH3:47])=[O:44]>ClCCl.C(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)C1C=CC=CC=1.Cl[Ru]Cl>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][C:22]=3[CH2:27][CH:28]=[CH:29][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH:42]([CH2:41][CH2:40][C:39]([F:38])([F:66])[C:56]([F:64])([F:65])[C:57]([F:62])([F:63])[C:58]([F:59])([F:61])[F:60])[C:43]([O:45][CH2:46][CH3:47])=[O:44])([CH3:20])[C@@H:18]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 22718077Ethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-decenoateHCID 694132253,17beta-Bis(benzyloxy)-11-(2-propenyl)estra-1,3,5(10),9(11)-tetraene

Produkt 1

HCID 86588531Ethyl 11-[3,17beta-bis(benzyloxy)estra-1,3,5(10), 9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoateAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 90332616Dichlororuthenium;tricyclohexyl-[phenyl-(tricyclohexyl-lambda5-phosphanyl)methyl]-lambda5-phosphaneKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzylidenebis(tricyclohexylphosphine)-dichlororuthenium (90 mg, 0.1 mmol) was added to a solution of 3,17β-bis(benzyloxy)-11-(2-propenyl)estra-1,3,5(10), 9(11)-tetraene (1.0 g, 2.0 mmol) and ethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-decenoate (1.81 g, 4.1 mmol) in dichloromethane (20 ml), followed by heating under reflux for 5 hours under nitrogen 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-[3,17β-bis(benzyloxy)estra-1,3,5(10), 9(11)-tetraen-11-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-undecenoate (863 mg, Yield 48%).

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours under nitrogen 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)

Quellen und Nachweise

ORD-Eintrag
ord-3a823937db5741d5acb4c261ae2f876c
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06737417B2

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