Water → 3-Hydroxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one

HRID 42276Notes

Reaction equation

HRID 42276 reaction equation
[Si]([O:8][C:9]1[C:10](=[O:15])[NH:11][CH:12]=[CH:13][CH:14]=1)(C(C)(C)C)(C)C.C([Li])CCC.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.O>C1COCC1>[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[C:10]2=[O:15])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 116371753-tert-Butyldimethylsilyloxy-1H-pyridin-2-oneHCID 178418339Butyllithium

Product 1

HCID 112770823-Hydroxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To stirred solution of 3-[(tert-butyldimethylsilyl)oxy]pyridin-2(1H)-one (1) (4.66 g, 20.7 mmol) in dry THF (150 mL), maintained at −78° C. under a dry nitrogen atmosphere is added n-butyl lithium (1.6 M solution in hexane, 21.0 mmol). After 20 minutes, 4-methyl-benzenesulfonyl chloride (3.95 g, 20.7 mmol) is added as a THF solution. The solution is allowed to warm to room temperature over one hour, the water (10 mL) is added and the contents of the reaction vessel is extracted with EtOAc (3×), washed with brine (1×), dried over Na2SO4 and concentrated. The combined organic layers are dried over Na2SO4 and concentrated. The residue is taken up in ethanol (10 mL) and treated with conc. HCl (2 mL). The mixture is allowed to stir for 1 hour and the solvent is removed under reduced pressure to afford the desired compound as a white solid. 1H NMR (300 MHz, DMSO) δ 2.43 (s, 3H), 6.14 (t, J=6.9 Hz, 1H), 6.76 (dd, J=7.65 Hz, 1.5 Hz, 1H), 7.18 (dd, J=6.6 Hz, 1.8 Hz, 1H), 7.32 (d, J=7.3 Hz, 2H), 7.98 (d, J=7.9 Hz, 2H).

Workup

  1. temperatureto warm to room temperature over one hour
  2. extractionthe contents of the reaction vessel is extracted with EtOAc (3×)
  3. washwashed with brine (1×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. dry with materialThe combined organic layers are dried over Na2SO4
  7. concentrationconcentrated
  8. additiontreated with conc. HCl (2 mL)
  9. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-17573190861b4814be83339b9eb6b5bb
Source dataset
uspto-grants-2013_09
Patent number
US08536181B2

Reaction notes

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