Tetrabutylammonium Fluoride → 3-(1-hydroxyethyl)-4-(pyridin-2-yl)-1H-isochromen-1-one

HRID 634377Notes

Reaction equation

HRID 634377 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH:27]([C:29]1[O:30][C:31](=[O:45])[C:32]2[C:37]([C:38]=1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH3:28])(C(C)(C)C)(C)C>C1COCC1.C(Cl)Cl.O>[OH:26][CH:27]([C:29]1[O:30][C:31](=[O:45])[C:32]2[C:37]([C:38]=1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH3:28]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1239811473-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-(pyridin-2-yl)-1H-isochromen-1-one2×

Product 1

HCID 1181313253-(1-hydroxyethyl)-4-(pyridin-2-yl)-1H-isochromen-1-oneYield 81.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.0 M TBAF in THF (1.43 mL, 1.43 mmol) was added dropwise to a solution of 3-(1-((tert-butyldimethylsilyl)oxy)ethyl)-4-(pyridin-2-yl)-1H-isochromen-1-one (intermediate B58.1, 0.394 g, 1.3 mmol) in THF (15 ml). The resulting mixture was stirred at RT for 2 hrs. The mixture was diluted with DCM and water was added. The mixture was extracted twice with DCM, the combined organic layers were dried over sodium sulfate and evaporated to dryness. The crude was purified by flash chromatography on silica gel Biotage cartridge (cyclohexane to cyclohexane:EtOAc=10:90) to afford title compound (0.284 g, 1.06 mmol)

Workup

  1. additionwas added
  2. extractionThe mixture was extracted twice with DCM
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude was purified by flash chromatography on silica gel Biotage cartridge (cyclohexane to cyclohexane:EtOAc=10:90)

Sources & evidence

ORD record
ord-48ce5e348c0c4bfe947e295d6752052c
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

Loading…