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

HRID 1875309Notes

Reaction equation

HRID 1875309 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-methylbenzenesulfonyl 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-3ece6b02f3694fea9dce1f19b1b3e977
Source dataset
uspto-grants-2012_11
Patent number
US08309537B2

Reaction notes

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