Potassium Carbonate → HCID 13527237, compound

HRID 730980Notes

Reaction equation

HRID 730980 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[CH2:12]([O:14][C:15](=[O:18])[CH2:16][SH:17])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:12]([O:14][C:15]([C:16]1[S:17][C:2]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=2[CH:4]=1)=[O:18])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 13527237HCID 13527237, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-fluoro-5-methoxy-benzaldehyde (4.35 g, 28.2 mmol) in DMF (30 mL) is added mercapto-acetic acid ethyl ester (3.71 mL, 33.9 mmol) and K2CO3 (7.86 g, 57.0 mmol). The resulting suspension is stirred at 80° C. for 60 min and quenched with water (300 mL). The mixture is extracted with EtOAc (2×200 mL), and the organic layer is dried over Na2SO4, concentrated, and purified by silica gel column chromatography (10% EtOAc/Hex), to give the title compound as an oil (4.40 g, 66%).

Workup

  1. customquenched with water (300 mL)
  2. extractionThe mixture is extracted with EtOAc (2×200 mL)
  3. dry with materialthe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (10% EtOAc/Hex)

Sources & evidence

ORD record
ord-1acdebc55c664670b926e7b2626b8cf6
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

Loading…