Methanesulfonate → alpha-Cyano-3-phenoxybenzyl 2-(2-benzothienyl)-3-methyl-butanoate

HRID 27926

Reaction equation

HRID 27926 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12].S([O-])(=O)(=O)C.[C:22]([CH:24](O)[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:26]=1)#[N:23].C(OCC)(=O)C.CCCCCC>C1COCC1.CN(C=O)C.C1COCC1.CCOCC>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([O:13][CH:24]([C:22]#[N:23])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:26]=1)=[O:12]

Participants

8

Reactant 4

HCID 85257MethanesulfonateHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 21226206Ethyl acetate hexaneHCID 233403922-(1-Benzothiophen-2-yl)-3-methylbutanoic acid

Product 1

HCID 23340427alpha-Cyano-3-phenoxybenzyl 2-(2-benzothienyl)-3-methyl-butanoate

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A mixture of 2-(2-benzothienyl)-3-methylbutanoic acid (0.5 g, 21.4 mmol) and KHCO3 (21.4 mmol) in 10 ml THF/DMF (1:1) is stirred for 10 minutes. Then the mesylate of α-cyano-3-phenoxybenzyl alcohol (0.65 g, 21.4 mmol) in 3 ml THF is added followed by stirring overnight. The mixture is diluted with 100 ml ether, washed with water and saturated NaCl, dried and solvent stripped to yield crude product. The product is isolated using thin layer chromatography developing with 15% ethyl acetate/hexane to give α-cyano-3-phenoxybenzyl 2-(2-benzothienyl)-3-methyl-butanoate, viscous liquid.

Workup

  1. stirringby stirring overnight
  2. washwashed with water and saturated NaCl
  3. customdried
  4. customto yield crude product
  5. customThe product is isolated

Sources & evidence

ORD record
ord-3e7d6f062fd54e5f8e5ba42178928462
Source dataset
uspto-grants-1980_09
Patent number
US04224330

Linked notes

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