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Diethyl [Chloro(cyano)methyl]phosphonate → 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-((Z)-2-chloro-2-cyanovinyl)-2,2-dimethylcyclopropanecarboxylate

HRID 554027
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 554027
CC(C)([O-])C.[K+].[CH3:7][C:8]1([CH3:30])[C@@H:10]([CH:11]=O)[C@H:9]1[C:13]([O:15][CH2:16][C:17]1[C:22]([F:23])=[C:21]([F:24])[C:20]([CH2:25][O:26][CH3:27])=[C:19]([F:28])[C:18]=1[F:29])=[O:14].C(OP([CH:39]([Cl:42])[C:40]#[N:41])(=O)OCC)C>O1CCCC1>[Cl:42]/[C:39](/[C:40]#[N:41])=[CH:11]\[C@@H:10]1[C@@H:9]([C:13]([O:15][CH2:16][C:17]2[C:22]([F:23])=[C:21]([F:24])[C:20]([CH2:25][O:26][CH3:27])=[C:19]([F:28])[C:18]=2[F:29])=[O:14])[C:8]1([CH3:7])[CH3:30]
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Komponenten

5

Edukt 3

HCID 10750995Diethyl [Chloro(cyano)methyl]phosphonateHCID 23665647Potassium tert-butoxideHCID 866391422,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-2,2-dimethyl-3-formylcyclopropanecarboxylate

Produkt 1

HCID 866391412,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-((Z)-2-chloro-2-cyanovinyl)-2,2-dimethylcyclopropanecarboxylateAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 0.14 g of potassium tert-butoxide in 1 ml of tetrahydrofuran was added dropwise to a mixture of 0.35 g of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-2,2-dimethyl-3-formylcyclopropanecarboxylate, 0.21 g of diethyl(chlorocyanomethyl)phosphonate and 5 ml of anhydrous tetrahydrofuran with ice-cooling under a nitrogen atmosphere. After stirring with ice-cooling for 15 minutes, the reaction mixture was poured into a saturated saline solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.13 g of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-((Z)-2-chloro-2-cyanovinyl)-2,2-dimethylcyclopropanecarboxylate represented by the formula (1):

Aufarbeitung

  1. temperaturecooling under a nitrogen atmosphere
  2. temperaturecooling for 15 minutes
  3. additionthe reaction mixture was poured into a saturated saline solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-81c8faf881574b0d91a1725f2768df66
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08048916B2

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