Pyridine → 3-Nitro-1-(4-octylphenyl)propyl acetate

HRID 1028874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028874
[N+:1]([CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=1)=[O:7])([O-:3])=[O:2].[BH4-].[Na+].N1C=CC=CC=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>CO.C(OCC)(=O)C.ClCCl>[C:30]([O:7][CH:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][CH:13]=1)[CH2:5][CH2:4][N+:1]([O-:3])=[O:2])(=[O:32])[CH3:31]

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 4311764Sodium borohydrideHCID 715785353-Nitro-1-(4-octylphenyl)propan-1-one

Produkt 1

HCID 569680573-Nitro-1-(4-octylphenyl)propyl acetateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-nitro-1-(4-octylphenyl)propan-1-one (12) (5.00 g) in methanol (25 ml) was added sodium borohydride (0.8 g) at 0° C. and the mixture was left at room temperature for 4.5 hr. The suspension was diluted with ethyl acetate and washed successively with 1 N HCl, sodium bicarbonate solution and brine. The ethyl acetate layer was dried over anhydrous Na2SO4 and concentrated. To the residue was added pyridine (1.5 eq), dichloromethane (10 v) and acetic anhydride (10 eq), and the mixture was left at room temperature overnight. To the reaction mixture was added ice water and the mixture was extracted with ethyl acetate and washed successively with 1 N HCl, sodium bicarbonate solution and brine. The ethyl acetate solution was dried over sodium sulfate and concentrated. The residue was pure enough for transformation to the next step or can be purified by silica gel column chromatography using hexane-ethyl acetate as eluent. Yield=94%, ESIMS 358.2 [M+Na]+

Aufarbeitung

  1. washwashed successively with 1 N HCl, sodium bicarbonate solution and brine
  2. dry with materialThe ethyl acetate layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. waitthe mixture was left at room temperature overnight
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed successively with 1 N HCl, sodium bicarbonate solution and brine
  7. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  8. concentrationconcentrated
  9. customcan be purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f3b36e9fa0b341099247f4ef291242e7
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735627B2

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