Dicyclohexylcarbodiimide → 5-benzyl-3-furyl-methyl (1R,trans) 2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate

HRID 485708

Reaktionsgleichung

C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:26])[C@H:19]([CH:20]=[C:21]=[CH2:22])[C@H:18]1[C:23]([OH:25])=[O:24].[CH2:27]([C:34]1[O:38][CH:37]=[C:36]([CH2:39]O)[CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:16][C:17]1([CH3:26])[C@H:19]([CH:20]=[C:21]=[CH2:22])[C@H:18]1[C:23]([O:25][CH2:39][C:36]1[CH:35]=[C:34]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:38][CH:37]=1)=[O:24]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

1.22 g of dicyclohexylcarbodiimide and a few crystals of 4-dimethylamino-pyridine were added at 0° C. to a solution of 900 mg of (1R,trans) 2,2-dimethyl-3-(1,2-propadienyl)cyclopropane-carboxylic acid in 20 ml of methylene chloride and the mixture was stirred at 0° C. for 15 minutes. A solution of 1.23 g of 5-benzyl-3-furyl-methanol in 7 ml of methylene chloride was added to the mixture which was stirred at 20° C. for 24 hours and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 3-7 petroleum ether (b.p.=35° to 70° C.)-benzene mixture and then a 7-3 petroleum ether (b.p.=35° to 70° C.)-benzene mixture yielded 825 mg of 5-benzyl-3-furyl-methyl (1R,trans) 2,2-dimethyl-3-(1,2-propadienyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =-24° (c= 0.6% in chloroform).

Aufarbeitung

stirringwas stirred at 20° C. for 24 hours
filtrationwas filtered
customThe filtrate was evaporated to dryness under reduced pressure
customthe residue was chromatographed over silica gel
washElution with a 3-7 petroleum ether (b.p.=35° to 70° C.)-benzene mixture

Quellen und Nachweise

ORD-Eintrag: ord-2e49d9d78be84755b202977f7a404eb0
Quelldatensatz: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04537897

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