Hydrochloric Acid → HCID 21914967, compound

HRID 2117890Notes

Reaction equation

HRID 2117890 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.N12CCCN=C1CCCC[CH2:16]2.IC.Cl>CN(C)C=O>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10](=[O:14])[C:11]([O:13][CH3:16])=[O:12])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21914987HCID 21914987, compound

Product 1

HCID 21914967HCID 21914967, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-(Methylsulfanyl)phenyl)-2-oxopropanoic acid (16.2 g), N,N-dimethylformamide (81 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (11.5 ml) were combined at 0° C. under nitrogen atmosphere. The mixture was stirred at the same temperature for an hour, and then iodomethane (9.59 ml) was added to the solution at the same temperature. The reaction mixture was stirred at room temperature for 4 hours, poured into 1N-hydrochloric acid, and extracted with ethyl acetate (twice). The combined organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with chloroform/ethyl acetate (30:1) as an eluent, and triturated with isopropyl ether/n-hexane to give methyl 3-(4-(methylsulfanyl)phenyl)-2-oxopropanoate (8.6 g) as a dark yellow solid.

Workup

  1. customwere combined at 0° C. under nitrogen atmosphere
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. extractionextracted with ethyl acetate (twice)
  4. washThe combined organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography over silica gel with chloroform/ethyl acetate (30:1) as an eluent
  8. customtriturated with isopropyl ether/n-hexane

Sources & evidence

ORD record
ord-cfb68f33f719484594f9a444d0456e8d
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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