Vinylcyclopentane → (3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-3-ethoxy-4-hydroxydihydrofuran-2(3H)-one

HRID 1670444

Reaktionsgleichung

Reaktionsgleichung von HRID 1670444
[CH2:1]([O:3][C@@H:4]1[C@H:8]([OH:9])[C@H:7]([C@H:10]([OH:13])[CH:11]=[CH2:12])[O:6][C:5]1=[O:14])[CH3:2].C([CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=C>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.C(Cl)Cl>[CH:17]1(/[CH:12]=[CH:11]/[C@H:10]([C@@H:7]2[O:6][C:5](=[O:14])[C@H:4]([O:3][CH2:1][CH3:2])[C@@H:8]2[OH:9])[OH:13])[CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

5

Edukt 2

HCID 77345VinylcyclopentaneHCID 57617787(3R,4R,5S)-3-ethoxy-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]dihydrofuran-2(3H)-one

Produkt 1

HCID 67329167(3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-3-ethoxy-4-hydroxydihydrofuran-2(3H)-oneAusbeute 12,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178479819HCID 178479819, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

550 mg of 51 (2.47 mmol), 0.987 g of vinylcyclopentane (10.26 mmol), 18 mL of CH2Cl2 and 63 mg of 2nd generation Grubb's catalyst (C46H65Cl2N2PRu, MW 848.98, 0.030 mmol) are added to a 50 mL round-bottomed flask. The medium is stirred for 24 h at RT and then the insoluble material is filtered and the solvent is evaporated. The crude product is chromatographed on a silica cartridge (40 g, eluent AcOEt/heptane—in an AcOEt gradient: 50 to 100%). 85 mg of expected product 52 are obtained.

Aufarbeitung

  1. filtrationthe insoluble material is filtered
  2. customthe solvent is evaporated
  3. customThe crude product is chromatographed on a silica cartridge (40 g, eluent AcOEt/heptane—in an AcOEt gradient

Quellen und Nachweise

ORD-Eintrag
ord-c919a1a57ab24fdf8a2c35a477930053
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994161B2

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