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Acetic Acid → (R)alpha-methyl-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propynyl]-cyclopropane-carboxylate

HRID 1719762
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1719762
[CH3:1][C:2]1([CH3:33])[C@@H:4]([C:5]#[C:6][C:7](=[O:14])[O:8]CC(Cl)(Cl)Cl)[C@H:3]1[C:15]([O:17][CH:18]([CH3:32])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16].C(O)(=O)C.O>C(Cl)Cl.[Zn]>[CH3:1][C:2]1([CH3:33])[C@@H:4]([C:5]#[C:6][C:7](=[O:8])[OH:14])[C@H:3]1[C:15]([O:17][C@H:18]([CH3:32])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:20]=1)=[O:16]
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Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 962WaterHCID 86740323alpha-methyl-3-phenoxyl-benzyl (1R,cis) 2,2-dimethyl-3-[3-oxo-3-(2,2,2-trichloroethoxy)-1-propynyl]-cyclopropane-carboxylate

Produkt 1

HCID 54097883(R)alpha-methyl-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propynyl]-cyclopropane-carboxylateAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994
Zinc
Katalysator
2×
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4.16 g of the product of Step A in 4 ml of methylene chloride was admixed with 45 ml of acetic acid containing 10% of water and 0.53 g of zinc powder and the mixture was stirred for 30 minutes at room temperature. then another 0.53 g of zinc powder were added 4 times until The reaction was complete and after 3 hours contact, the mixture was filtered. The filtrate was extracted with methylene chloride and the organic phase was washed with water, dried and evaporated to dryness by azeotropic distillation with toluene to obtain 3.05 g of (R)α-methyl-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propynyl]-cyclo-propane-carboxylate.

Aufarbeitung

  1. waitwas complete and after 3 hours
  2. filtrationcontact, the mixture was filtered
  3. extractionThe filtrate was extracted with methylene chloride
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness by azeotropic distillation with toluene

Quellen und Nachweise

ORD-Eintrag
ord-02283267819246ea8ca62666de8882c4
Quelldatensatz
uspto-grants-1985_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04542142

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