HCID 131721911, compound → HCID 18698767, compound

HRID 2289620Notes

Reaction equation

HRID 2289620 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:13]=[CH:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[O:20])[CH:9]=1)(C)(C)C>CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>[OH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[O:20])[CH:9]=1

Participants

4

Reactant 1

HCID 131721911HCID 131721911, compound

Product 1

HCID 18698767HCID 18698767, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

4-(Tert-butyl-dimethyl-silyloxymethyl)-1-phenyl-1H-pyridin-2-one from Step 3 (1.3 g) was dissolved in TBAF in 1M THF (15 mL). The clear reaction mixture was stirred for 16 hours. The reaction mixture was concentrated and purified on a column of silica eluting with 10% MeOH/EtOAc to yield 4-hydroxymethyl-1-phenyl-1H-pyridin-2-one as a tan solid. 1H NMR (400 MHz, CDCl3) δ 7.5-7.47 (m, 2H); 7.43 (d, 1H); 7.38-7.36 (m, 2H); 7.32-7.30 (d, 1H) 6.67 (s, 1H); 6.23 (d, 1H) 4.57 (d, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified on a column of silica eluting with 10% MeOH/EtOAc

Sources & evidence

ORD record
ord-4b5d7d96d2fc4dbbbbd14eb39fd0217d
Source dataset
uspto-grants-2000_07
Patent number
US06093737

Reaction notes

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