Acetyl chloride → 5-(4-(2-(Piperidin-1-yl)ethoxy)phenoxy)-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl acetate

HRID 445219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445219
[C:1](Cl)(=[O:3])[CH3:2].[F:5][C:6]([F:39])([F:38])[S:7]([O:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=2)[C:12]=1[O:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)(=[O:9])=[O:8].C(N(C(C)C)CC)(C)C>>[C:1]([O:21][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[CH:19][CH:20]=[C:11]([O:10][S:7]([C:6]([F:38])([F:5])[F:39])(=[O:9])=[O:8])[C:12]=2[O:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:27][CH:28]=2)[CH:17]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 866071646-Hydroxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonate

Produkt 1

HCID 583385445-(4-(2-(Piperidin-1-yl)ethoxy)phenoxy)-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl acetateAusbeute 90 %

Versuchsvorschrift

Add acetyl chloride (0.67 mL, 9.41 mmol) to a solution of 6-hydroxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl trifluoromethanesulfonate (2.4 g, 4.69 mmol) and diisopropylethylamine (2.45 mL, 14.05 mmol). Stir the mixture for 1 hour and then quench with aqueous sodium bicarbonate. Extract the mixture 3 times with dichloromethane. Combine the extracts, dry over sodium sulfate, filter, and concentrate to obtain the title compound (2.33 g, 4.22 mmol).

Aufarbeitung

  1. customquench with aqueous sodium bicarbonate
  2. extractionExtract the mixture 3 times with dichloromethane
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-b2291a587cc241779fce8f9f32bcad24
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476300B2

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