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 1582817Notes

Reaction equation

HRID 1582817 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 90332616Dichlororuthenium;tricyclohexyl-[phenyl-(tricyclohexyl-lambda5-phosphanyl)methyl]-lambda5-phosphaneCatalystHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-2eca54b5e463409a905cbb36788c1f34
Source dataset
uspto-grants-2004_05
Patent number
US06737417B2

Reaction notes

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