Dimethyl Sulfoxide → SB-200473

HRID 849699

Reaktionsgleichung

Reaktionsgleichung von HRID 849699
[Cl-].[Na+].O.CS(C)=O.C([CH:12]1[CH2:17][C:16]([C:32]#[N:33])([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:19]=2)[CH2:15][CH2:14][C:13]1=[O:34])(OC)=O>C(O)(C)C>[C:32]([C:16]1([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:19]=2)[CH2:17][CH2:12][C:13](=[O:34])[CH2:14][CH2:15]1)#[N:33]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 5234Sodium ChlorideHCID 10959646Methyl 5-cyano-5-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxocyclohexanecarboxylate

Produkt 1

HCID 9861604SB-200473

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

To a suspension of sodium chloride (315 g, 5.39 mol) and deionized water (315 mL) was added the dimethyl sulfoxide (4.2 L) solution of 2-carbomethoxy-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-one (323 g, 0.87 mol) and the resulting suspension was heated to 155° C. for 1.75 h. The reaction was cooled to 40° C., was quenched into 8 L of iced water (2° C.) and was extracted with ethyl acetate (3.5 L). The aqueous layer was isolated and re-extracted with 2.5 L of ethyl acetate. The combined organic extract (6 L) was washed two times with deionized water (2×1 L) and once with brine (1 L). The organic layer was isolated and concentrated in vacuo to afford a residue. This residue was dissolved in refluxing isopropanol (500 mL), was cooled to 0° C. and held at this temperature for 1 hour. The crystals were isolated by filtration, were washed with 250 mL of isopropanol (0° C.), and were dried in a vacuum oven (45° C. at 20 inches) to produce 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one. m.p. 111-112° C.; Anal. (C19H23NO3) calcd: C 72.82, H 7.40, N 4.47; found: C 72.72, H 7.39, N 4.48.

Aufarbeitung

  1. temperatureThe reaction was cooled to 40° C.
  2. customwas quenched into 8 L of iced water (2° C.)
  3. extractionwas extracted with ethyl acetate (3.5 L)
  4. customThe aqueous layer was isolated
  5. extractionre-extracted with 2.5 L of ethyl acetate
  6. extractionThe combined organic extract (6 L)
  7. washwas washed two times with deionized water (2×1 L)
  8. customThe organic layer was isolated
  9. concentrationconcentrated in vacuo
  10. customto afford a residue
  11. dissolutionThis residue was dissolved
  12. temperaturewas cooled to 0° C.
  13. customThe crystals were isolated by filtration
  14. washwere washed with 250 mL of isopropanol (0° C.)
  15. customwere dried in a vacuum oven (45° C. at 20 inches)

Quellen und Nachweise

ORD-Eintrag
ord-20699db7287f42a28f854b98ec54c5c7
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06013827

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