Aluminium lithium hydride → HCID 90406977, compound

HRID 1404178Notes

Reaction equation

HRID 1404178 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[C:8]2[C:16](OC)=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[C:1]1([N:7]2[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[C:8]2[CH2:16][OH:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90405307HCID 90405307, compound

Product 1

HCID 90406977HCID 90406977, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 1-phenyl-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate (460 mg, 1.71 mmol, 1.00 equiv) and tetrahydrofuran (4 mL). To the resulting mixture was then added a solution of LAH (135 mg, 3.56 mmol, 2.00 equiv) in tetrahydrofuran (1 mL) dropwise with stirring at 0° C. The resulting solution was stirred for 60 min at 0° C. in a water/ice bath. The reaction was then quenched by the addition of water (10 mL). The resulting solution was extracted with ethyl acetate (5×10 mL) and the organic layers combined. The resulting residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4) to yield [1-phenyl-3-(trifluoromethyl)-1H-pyrrol-2-yl]methanol as light yellow oil (280 mg, 66%).

Workup

  1. customInto a 25-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred for 60 min at 0° C. in a water/ice bath
  4. customThe reaction was then quenched by the addition of water (10 mL)
  5. extractionThe resulting solution was extracted with ethyl acetate (5×10 mL)

Sources & evidence

ORD record
ord-6afbcf281c424fad86b36bce880c72b5
Source dataset
uspto-grants-2014_12
Patent number
US08912227B1

Reaction notes

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