Potassium tert-butoxide → HCID 178516560, compound

HRID 1423955Notes

Reaction equation

HRID 1423955 reaction equation
[C:1]([C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11][C:12](=[O:16])N(C)C)(=[O:3])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1>[F:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:1]([OH:3])=[CH:2][C:12](=[O:16])[S:11]2

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86660141HCID 86660141, compound

Product 1

HCID 178516560HCID 178516560, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl-thiocarbamic acid S-(2-acetyl-3-fluoro-phenyl) ester (2.1 g, 8.7 mmol) was dissolved in anhydrous THF (25 mL.) This solution was slowly added to a rapidly stirring solution potassium tert-butoxide (22 mL, 1M, 22 mmol) via cannula. Upon complete addition, the reaction was permitted to stir overnight at ambient temperature. The reaction was concentrated in vacuo and the residue dissolved in water and extracted three times with an equal volume of 5:1 hexanes: ethyl acetate. The organic portions were discarded and the aqueous phase acidified with 1N HCl to precipitate the product. The product was isolated via filtration and dried to provide the title compound (1.59 g.) 1H NMR (200 MHz, DMSO-d6): δ (ppm)=12.192 (br s, 1H), 7.651-7.546 (m, 1H), 7.421 (d, 1H), 6.036 (s, 1H).

Workup

  1. additionUpon complete addition
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutionthe residue dissolved in water
  4. extractionextracted three times with an equal volume of 5:1 hexanes
  5. customto precipitate the product
  6. customThe product was isolated via filtration
  7. customdried

Sources & evidence

ORD record
ord-cd2a59fc1a8a401ab9fb157207c709c2
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

Loading…