Aluminium lithium hydride → HCID 59589426, compound

HRID 577177Notes

Reaction equation

HRID 577177 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([F:20])[C:14]=1[C:15](OCC)=[O:16])[CH3:8]>C1COCC1>[CH2:7]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([F:20])[C:14]=1[CH2:15][OH:16])[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59589366HCID 59589366, compound

Product 1

HCID 59589426HCID 59589426, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. mixture of lithium aluminum hydride (760 mg, 10.1 mmol) in anhydrous THF (60 mL) was slowly added a solution of ethyl 3-ethyl-5-fluoropyridine-4-carboxylate (2.00 g, 10.1 mmol) in anhydrous THF (25 mL). The reaction mixture was stirred at 0° C. for 2 hours. The reaction was quenched with 5N NaOH. Water (100 mL) and EtOAc (100 mL) were added. The mixture was stirred for 30 minutes. The solid material was removed by filtration. The organic layer was recovered. The aqueous layer was extracted with EtOAc (1×100 mL). The combined organic extracts were dried over MgSO4, filtered, evaporated and dried in vacuo, affording (3-ethyl-5-fluoropyridin-4-yl)methanol (1.5 g, 95% yield). The product was used without further purification.

Workup

  1. customThe reaction was quenched with 5N NaOH
  2. additionWater (100 mL) and EtOAc (100 mL) were added
  3. stirringThe mixture was stirred for 30 minutes
  4. customThe solid material was removed by filtration
  5. customThe organic layer was recovered
  6. extractionThe aqueous layer was extracted with EtOAc (1×100 mL)
  7. dry with materialThe combined organic extracts were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customdried in vacuo

Sources & evidence

ORD record
ord-cd8a9f3052614b98babf018850407338
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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