Formaldehyde → 2-Butyl-4-chloro-6-fluoro-5-methoxy-1-indanone

HRID 7895

Reaktionsgleichung

Reaktionsgleichung von HRID 7895
[Cl:1][C:2]1[CH:3]=[C:4]([C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]=[C:6]([F:10])[C:7]=1[O:8][CH3:9].C=O.[C:20](=O)([O-])[O-].[K+].[K+]>CO>[CH2:13]([CH:12]1[CH2:20][C:3]2[C:4](=[CH:5][C:6]([F:10])=[C:7]([O:8][CH3:9])[C:2]=2[Cl:1])[C:11]1=[O:17])[CH2:14][CH2:15][CH3:16]

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 219909381-(3-Chloro-5-fluoro-4-methoxyphenyl)-1-hexanone

Produkt 1

HCID 219908612-Butyl-4-chloro-6-fluoro-5-methoxy-1-indanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of the crude 1-(3-chloro-5-fluoro-4-methoxyphenyl)-1-hexanone from step 1, methanol (8.7 mL), 37% aqueous formaldehyde (0.786 mL, 10.5 mmol), and potassium carbonate (1.2 g, 8.72 mmol) was stirred and heated in an oil bath at 50° C. for 7 hours. The mixture was evaporated under vacuum and the residue partitioned between EtOAc (100 mL) and water (100 mL) containing 2N HCl (10 mL). The organic phase was washed with brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (1.86 g) consisting of predominantly 1-(3-chloro-5-fluoro-4-methoxyphenyl)-2-(methoxymethyl)-1-hexanone.

Aufarbeitung

  1. customThe mixture was evaporated under vacuum
  2. customthe residue partitioned between EtOAc (100 mL) and water (100 mL)
  3. additioncontaining 2N HCl (10 mL)
  4. washThe organic phase was washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum to an oil (1.86 g)

Quellen und Nachweise

ORD-Eintrag
ord-644c4332f59e457193dc2c4b5fdfdc26
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087599B2

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