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Hexane → trans-N-(4'-chlorophenyl)-2,2-diethoxy-3,6-dimethyl-4-ethoxy-3,4-dihydro-2H-pyran-5-carboxamide

HRID 466275
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 466275
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[C:10](=[CH:14][O:15][CH2:16][CH3:17])[C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=1.[CH2:19]([O:21][C:22]([O:25][CH2:26][CH3:27])=[CH:23][CH3:24])[CH3:20].CCCCCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:10]2[C@@H:14]([O:15][CH2:16][CH3:17])[C@H:23]([CH3:24])[C:22]([O:25][CH2:26][CH3:27])([O:21][CH2:19][CH3:20])[O:13][C:11]=2[CH3:12])=[O:18])=[CH:6][CH:7]=1
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Komponenten

5

Edukt 3

HCID 8058HexaneHCID 1408411-Propene, 1,1-diethoxy-HCID 54471103N-(4'-Chlorophenyl)-2-ethoxymethylene-3-oxobutanamide

Produkt 1

HCID 86746200trans-N-(4'-chlorophenyl)-2,2-diethoxy-3,6-dimethyl-4-ethoxy-3,4-dihydro-2H-pyran-5-carboxamideAusbeute 31,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140Toluene
Lösungsmittel

Versuchsvorschrift

N-(4'-Chlorophenyl)-2-ethoxymethylene-3-oxobutanamide (1.3 g) was stirred in toluene (10 ml) whilst 1,1-diethoxyprop-1-ene (2 g) was added dropwise. The mixture was stirred at room temperature for 40 hours and evaporated to dryness. The residual gum was purified by medium pressure liquid chromatography on K60 silica using ethyl acetate/petroleum ether b.p. 60°-80° C. 15/85 v/v as eluting solvent to give two stereoisomers. The first isomer after trituration with n-hexane gave trans-N-(4'-chlorophenyl)-2,2-diethoxy-3,6-dimethyl-4-ethoxy-3,4-dihydro-2H-pyran-5-carboxamide (0.6 g), m.p. 104°-106° C. The n.m.r. spectrum (deuterochloroform) showed the --CH(OEt)-- signal at 4.0 ppm (doublet of quartets 1H, J=3 Hz and 1 Hz), consistent with the transconfiguration. The second isomer, after trituration with n-hexane, gave cis-N-(4'-chlorophenyl)-2,2-diethoxy-3,6-dimethyl-4-ethoxy-3,4-dihydro-2H-pyran-5-carboxamide (0.1 g), m.p. 125°-7° C. The n.m.r. spectrum (deuterochloroform) showed the --CH(OEt)--signal at 4.5 ppm (doublet of quartets, 1H, J=7 Hz and 1 Hz) consistent with the cis-configuration.

Aufarbeitung

  1. additionwas added dropwise
  2. customevaporated to dryness
  3. customThe residual gum was purified by medium pressure liquid chromatography on K60 silica
  4. wash15/85 v/v as eluting solvent
  5. customto give two stereoisomers

Quellen und Nachweise

ORD-Eintrag
ord-5b00e9d8bae743c7818c6fc4e60bfd5d
Quelldatensatz
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05155236

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