Potassium Carbonate → HCID 89767995, compound

HRID 591567Notes

Reaction equation

HRID 591567 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:10])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.Br[CH:12]([CH3:20])[C:13](=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:10][CH:12]([CH3:20])[C:13](=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 22504773HCID 22504773, compound

Product 1

HCID 89767995HCID 89767995, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-chloro-5-methoxybenzenethiol (1.90 g), methyl 4-bromo-3-oxopentanoate (2.50 g) and K2CO3 (1.80 g) in DMF (dry) (36.3 mL) was stirred at room temperature overnight. The reaction was quenched with H2O and diluted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (2.09 g).

Workup

  1. customThe reaction was quenched with H2O
  2. additiondiluted with EtOAc
  3. customThe organic layer was separated
  4. washwashed successively with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-049b59cc684f41df97646494a5e80a90
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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