Diazomethane → Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxypentanoate

HRID 463550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 463550
[N+](=[CH2:3])=[N-].[F:4][C:5]([F:31])([F:30])[C:6]1[CH:29]=[CH:28][C:9]([O:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][CH:16]([CH3:25])[CH:17]([OH:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1>CCOCC>[F:4][C:5]([F:30])([F:31])[C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][CH:16]([CH3:25])[CH:17]([O:24][CH3:3])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[CH:28][CH:29]=1

Komponenten

4

Edukt 2

HCID 9550DiazomethaneHCID 12856783Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoate

Produkt 1

HCID 13488554Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxypentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Diazomethane (2.8 g) in ether (100 ml) is added to ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoate (1.88 g, 3.75 mmol) in ether (5 ml) under N2 and in an ice bath. Small amounts of chromatographic silica gel are added to the mixture in the ice bath until the color disappears. The mixture is then stirred overnight with cooling. The silica gel is removed by filtration and the organic phase is dried and concentrated. The crude product is purified by preparative thin layer chromatography to yield ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxypentanoate (cpd. 1 in Table A). MS m/e 412 (m+).

Aufarbeitung

  1. temperaturewith cooling
  2. customThe silica gel is removed by filtration
  3. customthe organic phase is dried
  4. concentrationconcentrated
  5. customThe crude product is purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a5ecd829d2c64042b14c2927f14178f8
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04520199

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