4-Methyl-2,3,5,6-tetrafluorobenzyl alcohol → 4-methyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 384422

Reaktionsgleichung

Reaktionsgleichung von HRID 384422
[CH3:1][C:2]1[C:9]([F:10])=[C:8]([F:11])[C:5]([CH2:6][OH:7])=[C:4]([F:12])[C:3]=1[F:13].[C:14]([C:16]([CH3:26])=[CH:17][C@@H:18]1[C@@H:20]([C:21](O)=[O:22])[C:19]1([CH3:25])[CH3:24])#[N:15]>CN(C)C1C=CN=CC=1.ClCCl>[C:14]([C:16]([CH3:26])=[CH:17][C@@H:18]1[C@@H:20]([C:21]([O:7][CH2:6][C:5]2[C:4]([F:12])=[C:3]([F:13])[C:2]([CH3:1])=[C:9]([F:10])[C:8]=2[F:11])=[O:22])[C:19]1([CH3:25])[CH3:24])#[N:15]

Komponenten

5

Edukt 2

HCID 27342094-Methyl-2,3,5,6-tetrafluorobenzyl alcoholHCID 66664531(1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid

Produkt 1

HCID 866520784-methyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylateAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, 0.59 g of N,N-dicyclohexyl carbodiimide was added to a mixture of 0.55 g of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol, 0.51 g of (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid, 0.10 g of 4-dimethylaminopyridine and 7 ml of anhydrous dichloromethane, and the mixture was stirred at room temperature for 3 hours. Thereafter, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.72 g of 4-methyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate represented by the following formula:

Aufarbeitung

  1. filtrationThereafter, the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cc6cd7692ab64668aa9d164cd4b57dc8
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367724B2

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