Dimethylformamide → 3-Phenoxybenzyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate

HRID 27931

Reaction equation

HRID 27931 reaction equation
CN(C=O)C.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13]([CH:15]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:18])=[O:17])=[CH:12][C:11]=2[CH:22]=1.C([O-])([O-])=O.[K+].[K+].[O:29]([C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH2:39]Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CCOCC>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13]([CH:15]([CH:19]([CH3:20])[CH3:21])[C:16]([O:18][CH2:39][C:38]3[CH:41]=[CH:42][CH:43]=[C:36]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:37]=3)=[O:17])=[CH:12][C:11]=2[CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 542046732-(5-Chloro-2-benzothienyl)-3-methylbutanoic acid

Product 1

HCID 544776893-Phenoxybenzyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 20 ml DMF, 2-(5-chloro-2-benzothienyl)-3-methylbutanoic acid (0.5 g), K2CO3 (0.51 g) and 3-phenoxybenzyl bromide (0.44 g) is stirred, under nitrogen, for about 15 hours. The mixture is then taken up in ether, washed with water and brine, dried over Na2SO4 and solvent removed. The crude product is plated developing with 10% ether/hexane to give 3-phenoxybenzyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4 and solvent
  3. customremoved

Sources & evidence

ORD record
ord-afd7ba97cc11477984f0728908ef7c09
Source dataset
uspto-grants-1980_09
Patent number
US04224330

Linked notes

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