1-Methylimidazole → 2,3,5,6-tetrafluorobenzyl (1R,3R)-3-((E)-Buta-1,3-dienyl)-2,2-dimethylcyclopropane-1-carboxylate

HRID 1770358

Reaktionsgleichung

Reaktionsgleichung von HRID 1770358
[CH:1](/[C@@H:5]1[C@@H:7]([C:8]([OH:10])=[O:9])[C:6]1([CH3:12])[CH3:11])=[CH:2]\[CH:3]=[CH2:4].CN1C=CN=C1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[F:30][C:31]1[C:38]([F:39])=[CH:37][C:36]([F:40])=[C:35]([F:41])[C:32]=1[CH2:33]O>CC#N>[CH:1](/[C@@H:5]1[C@@H:7]([C:8]([O:10][CH2:33][C:32]2[C:35]([F:41])=[C:36]([F:40])[CH:37]=[C:38]([F:39])[C:31]=2[F:30])=[O:9])[C:6]1([CH3:12])[CH3:11])=[CH:2]\[CH:3]=[CH2:4]

Komponenten

6

Edukt 4

HCID 13901-MethylimidazoleHCID 73974-Toluenesulfonyl chlorideHCID 27340292,3,5,6-Tetrafluorobenzyl alcoholHCID 86644402(1R,3R)-3-((E)-buta-1,3-dienyl)-2,2-dimethylcyclopropane-1-carboxylic acid

Produkt 1

HCID 252077732,3,5,6-tetrafluorobenzyl (1R,3R)-3-((E)-Buta-1,3-dienyl)-2,2-dimethylcyclopropane-1-carboxylateAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel3×

Versuchsvorschrift

In a similar way to that described in example 1 part b., 2.38 g (14.3 mmol) of (1R,3R)-3-((E)-buta-1,3-dienyl)-2,2-dimethylcyclopropane-1-carboxylic acid are added with 3.4 ml (43 mmol) of N-methyl imidazole dissolved in 43 ml of CH3CN, and reacted with 3.26 g (17.2 mmol) of tosyl chloride dissolved in 19 ml of CH3CN then with 2.6 ml (14.3 mmol) of 2,3,5,6-tetrafluorobenzyl alcohol dissolved in 16 ml of CH3CN. After purification on silica gel column with 100/1 (v/v) petroleum ether/ethyl ether as eluent, 4.58 g of an oily product with an E/Z ratio of 97/3 and a purity equal to 96.1% are obtained.

Aufarbeitung

  1. customAfter purification on silica gel column with 100/1 (v/v) petroleum ether/ethyl ether as eluent

Quellen und Nachweise

ORD-Eintrag
ord-4f24a3ed780b4e6bb05e69fa761dfa67
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09247750B2

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