Ethanol → HCID 23157612, compound

HRID 2110872Notes

Reaction equation

HRID 2110872 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)[N:7]([CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24](OC)=[O:25])=[CH:22][CH:21]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.[Cl-].[NH4+]>O1CCCC1>[C:1]([C:5]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)[N:7]([CH2:19][C:20]2[CH:29]=[CH:28][C:23]([CH2:24][OH:25])=[CH:22][CH:21]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23159944HCID 23159944, compound

Product 1

HCID 23157612HCID 23157612, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (20 mL) of methyl 4-({3-tert-butyl-5-[(6-methylpyridin-2-yl)methoxy]-1H-pyrazol-1-yl}methyl)benzoate (2.14 g, 5.44 mmol) in tetrahydrofuran was added lithium aluminum hydride (0.26 g, 5.5 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Ethanol (10 mL) and saturated aqueous ammonium chloride solution (1.0 mL) were added to the reaction mixture. The precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography (ethyl acetate:hexane=3:1) to give the title compound (1.86 g, yield 94%) as a yellow oil. 1H NMR (CDCl3) δ: 1.26 (9H, s), 2.24 (1H, br s), 2.53 (3H, s), 4.64 (2H, br s), 5.09 (2H, s), 5.17 (2H, s), 5.43 (1H, s), 6.97-7.08 (2H, m), 7.10-7.16 (2H, m), 7.23-7.30 (2H, m), 7.51 (1H, t, J=7.8 Hz).

Workup

  1. temperaturecooling
  2. filtrationThe precipitated insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b35a3276b0f6491c9958e4ca46bdded7
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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