Methanol → HCID 178519885, compound

HRID 1162754Notes

Reaction equation

HRID 1162754 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:7]([C:8](OCC)=[O:9])=[CH:6][NH:5][N:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CO.CCOC(C)=O>C1COCC1>[F:14][C:2]([F:1])([F:13])[C:3]1[C:7]([CH2:8][OH:9])=[CH:6][NH:5][N:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 178469923HCID 178469923, compound

Product 1

HCID 178519885HCID 178519885, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (5.00 g, 24 mmol) was dissolved in dry THF (50 mL). LiAlH4 (912 mg, 24.4 mmol) was added portionwise with care. The reaction mixture was stirred at RT for 3 h. MeOH (50 mL) was added dropwise and stirring continued for 30 min before concentrating in vacuo to give an off white solid. EtOAc (50 mL) was added and the solid was stirred for 30 min before filtering. The filtrate was concentrated and this procedure was repeated 4 times before the filtrates, after concentration in vacuo, were combined and purified by flash column chromatography (silica gel; eluent EtOAc:heptane, 4:1) to give the desired product (2.1 g, 12.6 mmol, 53%).

Workup

  1. stirringstirring
  2. waitcontinued for 30 min
  3. concentrationbefore concentrating in vacuo
  4. customto give an off white solid
  5. stirringthe solid was stirred for 30 min
  6. filtrationbefore filtering
  7. concentrationThe filtrate was concentrated
  8. concentrationafter concentration in vacuo
  9. custompurified by flash column chromatography (silica gel; eluent EtOAc:heptane, 4:1)

Sources & evidence

ORD record
ord-3778798bd5a74053aa47ffde84de3852
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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