Acetyl chloride → (RS) alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(3-oxo-3-methoxymethyl-1-propynyl)-cyclopropane-carboxylate

HRID 1639431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639431
[CH3:1][C:2]1([CH3:29])[C@@H:4]([C:5]#[C:6][C:7](O)=[O:8])[C@H:3]1[C:10]([O:12][CH:13]([C:27]#[N:28])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:11].[H-].[Na+].Cl[CH2:33][O:34][CH2:35]Cl.COCOC.C(Cl)(=O)C.P(O)(O)([O-])=O.[Na+]>CN(C)C=O.CO>[CH3:29][C:2]1([CH3:1])[C@@H:4]([C:5]#[C:6][C:7](=[O:8])[CH2:33][O:34][CH3:35])[C@H:3]1[C:10]([O:12][CH:13]([C:27]#[N:28])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)=[O:11]

Komponenten

9

Edukt 6

HCID 6367Acetyl chlorideHCID 8020DimethoxymethaneHCID 10967Bis(Chloromethyl) EtherHCID 24758Sodium hydrideHCID 23672064Monosodium phosphateHCID 53972231(RS)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(3-hydroxy-3-oxo-1-propynyl)-cyclopropane-carboxylate

Produkt 1

HCID 54554474(RS) alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(3-oxo-3-methoxymethyl-1-propynyl)-cyclopropane-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3 g of (RS)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(3-hydroxy-3-oxo-1-propynyl)-cyclopropane-carboxylate in 30 ml of anhydrous dimethylformamide was cooled to +10° C. and 300 mg of 61% sodium hydride in oil were added in portions thereto. Then, over 15 minutes, 2.5 ml of chloromethyl ether solution prepared by mixing 4.5 ml of methylal and 0.52 ml of methanol and slowly adding 3.53 ml of acetyl chloride after which the mixture was stirred for 36 hours at room temperature. The mixture was stirred for 2 hours and was then poured into an aqueous solution of monosodium phosphate. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and eluted with a 75-25 mixture of cyclohexane-ethyl acetate to obtain 2 g of (RS) α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(3-oxo-3-methoxymethyl-1-propynyl)-cyclopropane-carboxylate.

Aufarbeitung

  1. stirringThe mixture was stirred for 2 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was chromatographed over silica gel
  7. washeluted with a 75-25 mixture of cyclohexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c4933f73e7d84f4990280ee1df2f0c41
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04883806

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