Phosphorus Pentoxide-Methanesulfonic Acid → Methyl 2-[6-methoxy-4-(trifluoromethyl)benzo[b]thiophen-3-yl]acetate

HRID 591437Notes

Reaction equation

HRID 591437 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:13][CH2:14][C:15](=O)[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[CH3:20][O:19][C:17](=[O:18])[CH2:16][C:15]1[C:6]2[C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[S:13][CH:14]=1

Participants

4

Reactant 2

HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidHCID 89768260Methyl 4-((3-methoxy-5-(trifluoromethyl)phenyl)sulfanyl)-3-oxobutanoate

Product 1

HCID 121004362Methyl 2-[6-methoxy-4-(trifluoromethyl)benzo[b]thiophen-3-yl]acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-((3-methoxy-5-(trifluoromethyl)phenyl)sulfanyl)-3-oxobutanoate (810 mg) was added to Eaton's reagent (1994 μl) at room temperature for 2 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was subjected to silica gel column chromatography (EtOAc/hexane) to give methyl(6-methoxy-4-(trifluoromethyl)-1-benzothiophen-3-yl)acetate as a crude product (604 mg). The product was used to the next step without further purification.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ef2df80ec7c4caba964a7d909c36546
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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