Trifluoroacetic acid → 2-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone

HRID 61309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 61309
[O:1]=[C:2]([C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:20]=1)[CH2:3][C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6]CC(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[OH:6][C:5]1[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=1[CH2:3][C:2]([C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:20]=1)=[O:1]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86691091t-butyl 2-(2-(2-oxo-2-(1-pentyl-1H-indol-3-yl)ethyl)phenoxy)acetate2×

Produkt 1

HCID 866910902-(2-hydroxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanoneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

t-Butyl 2-(2-(2-oxo-2-(1-pentyl-1H-indol-3-yl)ethyl)phenoxy)acetate (O-desmethyl JWH-250 t-butyl 2-CME) 6 (1.09 g, 2.50 mmol) was dissolved in dichloromethane (20 ml) and trifluoroacetic acid (10 ml) was added and the reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was purified by column chromatography (Biotage Isolera 4, SNAP-50 g, 50% ethyl acetate in hexane) to give 512 mg (54%) of O-desmethyl JWH-250 2-CME (Hapten 1) as a tan solid.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography (Biotage Isolera 4, SNAP-50 g, 50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-786b7da843d2405b9b0be44890d3e808
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441033B2

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