Ethanol → HCID 23157444, compound

HRID 2110870Notes

Reaction equation

HRID 2110870 reaction equation
[CH2:1]([O:8][C:9]1[N:13]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19](OC)=[O:20])=[CH:17][CH:16]=2)[N:12]=[C:11]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]1[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:23][CH:24]=2)[N:12]=[C:11]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23157233HCID 23157233, compound

Product 1

HCID 23157444HCID 23157444, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-([5-(benzyloxy)-3-tert-butyl-1H-pyrazol-1-yl]methyl]benzoate (2.14 g, 5.65 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (0.27 g, 5.7 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=1:1) to give the title compound (1.97 g, yield 99%) as a colorless oil. 1H NMR (CDCl3) δ: 1.28 (9H, s), 1.77 (1H, br t), 4.62-4.70 (2H, m), 5.00 (2H, s), 5.13 (2H, s), 5.47 (1H, s), 7.08-7.38 (9H, m).

Workup

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

Sources & evidence

ORD record
ord-fae46c013a8741878fc41f8e54de018c
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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