Sodium sulfate decahydrate → HCID 22244691, compound

HRID 891153Notes

Reaction equation

HRID 891153 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([CH3:19])[N:10]([C:20]2[CH:30]=[CH:29][C:23]([C:24](OCC)=[O:25])=[CH:22][N:21]=2)[N:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[F-].[K+]>O1CCCC1>[CH3:7][C:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:11]([CH3:19])[N:10]([C:20]2[N:21]=[CH:22][C:23]([CH2:24][OH:25])=[CH:29][CH:30]=2)[N:9]=1

Participants

6

Reactant 4

HCID 62649Sodium sulfate decahydrateHCID 522689Potassium FluorideHCID 21226445Aluminium lithium hydrideHCID 22244651HCID 22244651, compound

Product 1

HCID 22244691HCID 22244691, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of lithium aluminum hydride (0.72 g, 15.1 mmol) and tetrahydrofuran (20 mL) was added slowly a solution of ethyl 6-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)nicotinate (step 1, 2.43 g, 7.56 mmol) and tetrahydrofuran (40 mL) at 0° C. After 2 h, sodium sulfate decahydrate and potassium fluoride were added slowly to the mixture at 0° C. The mixture was filtered through a bed of celite, and the filtrate was concentrated in vacuo. The residue was purified by silica-gel column chromatography eluting with hexane/ethyl acetate (1:1) to give 1.51 g (72%) of title compound as white solids: MS (ESI) m/z 280 [M+H]+, 1H-NMR (CDCl3) δ 8.42-8.41 (1H, m), 7.83-7.82 (2H, m), 7.47-7.28 (5H, m), 4.75 (2H, s), 2.58 (3H, s), 2.33 (3H, s), 2.30 (3H, s).

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica-gel column chromatography
  4. washeluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-76789a82dffa411fb43042bcdf65691f
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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