Methanol → HCID 67084577, compound

HRID 2103610Notes

Reaction equation

HRID 2103610 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH2:7]([O:9][C:10](=[O:26])/[C:11](/[C:19]1[S:20][C:21](SC)=[CH:22][CH:23]=1)=[CH:12]/[CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH3:8].[CH3:27]O>O>[CH2:7]([O:9][C:10](=[O:26])/[C:11](/[C:19]1[S:20][C:21]([S:3]([CH3:27])(=[O:5])=[O:2])=[CH:22][CH:23]=1)=[CH:12]/[CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH3:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 67084693HCID 67084693, compound

Product 1

HCID 67084577HCID 67084577, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add a suspension of oxone® (2.07 g, 3.37 mmol) in water (10 mL) to a solution of (Z)-4-cyclopentyl-2-(5-methylsulfanyl-thiophen-2-yl)-but-2-enoic acid ethyl ester (804 mg, 2.59 mmol) in methanol (14 mL). Stir for 1 h, monitor completion of the reaction by LCMS. Filter the reaction mixture, concentrate the filtrate and extract the residue with dichloromethane. Combine the extracts, wash them with saturated aqueous sodium chloride solution, dry them over sodium sulfate, and remove solvent under vacuum to give 939 mg of the product. MS (m/e): 343.0 (M+H).

Workup

  1. additionAdd
  2. customcompletion of the reaction by LCMS
  3. filtrationFilter the reaction mixture
  4. concentrationconcentrate the filtrate
  5. extractionextract the residue with dichloromethane
  6. washwash them with saturated aqueous sodium chloride solution
  7. dry with materialdry them over sodium sulfate
  8. customremove solvent under vacuum

Sources & evidence

ORD record
ord-9c10d4e41e85482bb88f958212b84d30
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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