Potassium Carbonate → HCID 67272809, compound

HRID 599690Notes

Reaction equation

HRID 599690 reaction equation
[CH2:1]([C:3]([C:6]1[CH:7]=[CH:8][C:9](F)=[C:10]([CH:13]=1)[CH:11]=O)=[CH:4][CH3:5])[CH3:2].[CH2:15]([O:17][C:18](=[O:21])[CH2:19][SH:20])[CH3:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:15]([O:17][C:18]([C:19]1[S:20][C:9]2[CH:8]=[CH:7][C:6]([C:3]([CH2:1][CH3:2])=[CH:4][CH3:5])=[CH:13][C:10]=2[CH:11]=1)=[O:21])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 76579095HCID 76579095, compound

Product 1

HCID 67272809HCID 67272809, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-(1-ethyl-propenyl)-2-fluoro-benzaldehyde (8.70 g, 45.3 mmol) in DMF (40 mL) is treated with mercapto-acetic acid ethyl ester (8.16 g, 67.9 mmol) and K2CO3 (12.5 g, 90.6 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 using silica gel column chromatography (6% EtOAc/Hex), to give the title compound as an oil (11.0 g, 89%).

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

Sources & evidence

ORD record
ord-a95ffb48707d40e68a7c53eb4a7fd524
Source dataset
uspto-grants-2011_03
Patent number
US07897789B2

Reaction notes

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