Triethylamine → 4-Fluoro-3-phenoxybenzyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate

HRID 27933Notes

Reaction equation

HRID 27933 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.[Cl:24][C:25]1[CH:26]=[CH:27][C:28]2[S:32][C:31]([CH:33]([CH:37]([CH3:39])[CH3:38])[C:34](O)=[O:35])=[CH:30][C:29]=2[CH:40]=1>CCOCC>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]2[S:32][C:31]([CH:33]([CH:37]([CH3:38])[CH3:39])[C:34]([O:7][CH2:6][C:5]3[CH:8]=[CH:9][C:2]([F:1])=[C:3]([O:10][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:4]=3)=[O:35])=[CH:30][C:29]=2[CH:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12874224(4-Fluoro-3-phenoxyphenyl)methanolHCID 542046732-(5-Chloro-2-benzothienyl)-3-methylbutanoic acid

Product 1

HCID 541134734-Fluoro-3-phenoxybenzyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 4-fluoro-3-phenoxybenzyl alcohol (0.22 g, 0.99 mmol) and triethylamine (0.14 g, 1.38 mmol) in ether (about 15 ml), under nitrogen, is added by syringe a solution of the acid chloride of 2-(5-chloro-2-benzothienyl)-3-methylbutanoic acid (1.5 mmol) in ether. The mixture is stirred for about 1 hour and then quenched with saturated aqueous sodium bicarbonate. The ether phase is washed with aqueous sodium bicarbonate, water and brine and filtered through silica. Evaporation of solvent, followed by thin layer chromatography, gives 4-fluoro-3-phenoxybenzyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate.

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. washThe ether phase is washed with aqueous sodium bicarbonate, water and brine
  3. filtrationfiltered through silica
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-898488c243e84b2bad3076dfea519478
Source dataset
uspto-grants-1980_09
Patent number
US04224330

Reaction notes

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