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

HRID 445219Notes

Reaction equation

HRID 445219 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b2291a587cc241779fce8f9f32bcad24
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

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