p-Toluenesulfonic acid → (S)alpha-cyano-3-phenoxy-4-fluoro-benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylate

HRID 1719768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1719768
[CH3:1][C:2]1([CH3:34])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:13])[O:8]C(C)(C)C)[C@H:3]1[C:14]([O:16][C@H:17]([C:32]#[N:33])[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:19]=1)=[O:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:34])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:8])[OH:13])[C@H:3]1[C:14]([O:16][C@H:17]([C:32]#[N:33])[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:19]=1)=[O:15]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 13188405(S)alpha-cyano-3-phenoxy-4-fluoro-benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-tert.-butoxy-1-propenyl]-cyclopropanecarboxylate

Produkt 1

HCID 86740328(S)alpha-cyano-3-phenoxy-4-fluoro-benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylateAusbeute 106,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 350 g of the product of Step A, 35 g of p-toluene sulfonic acid and 3.5 liters of toluene was refluxed for 45 minutes and was then cooled, washed with water, dried and evaporated to dryness under reduced pressure to obtain 328 g of (S)α-cyano-3-phenoxy-4-fluoro-benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylate.

Aufarbeitung

  1. temperaturewas refluxed for 45 minutes
  2. temperaturewas then cooled
  3. washwashed with water
  4. customdried
  5. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-236f5bc2709a4380a79d7c9ab29598f1
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04542142

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