Potassium tert-butoxide → HCID 178516555, compound

HRID 1746202Notes

Reaction equation

HRID 1746202 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[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:7]1[CH:6]=[C:5]2[C:4]([C:1]([OH:3])=[CH:2][C:12](=[O:16])[S:11]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86660133HCID 86660133, compound

Product 1

HCID 178516555HCID 178516555, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dimethyl-thiocarbamic acid S-(2-acetyl-5-fluoro-phenyl) ester (2.7 g, 11.2 mmol) was dissolved in dry THF (15 mL) and transferred via cannula to a flask containing 1M potassium tert-butoxide in THF (22.4 mL). The reaction was permitted to for 4 h at ambient temperature. The reaction mixture was concentrated in vacuo and dissolved in water. The aqueous layer was extracted with diethyl ether and the organic phase was discarded. The aqueous portion was acidified to pH 3 with 1N HCl, the precipitate collected via filtration and air dried to provide 7-fluoro-4-hydroxy-thiochromen-2-one (2.0 g, 91%) which was used without further purification. MS ESI(−) m/e: 195.209 (M−1).

Workup

  1. customtransferred via cannula to a flask
  2. customwas permitted to for 4 h at ambient temperature
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in water
  5. extractionThe aqueous layer was extracted with diethyl ether
  6. filtrationthe precipitate collected via filtration and air
  7. customdried

Sources & evidence

ORD record
ord-14d852283bb641429718bff29b2757cd
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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