Aluminium lithium hydride → 1-(3-Pyridinyl)cyclopropanemethanol

HRID 993253Notes

Reaction equation

HRID 993253 reaction equation
C[O:2][C:3]([C:5]1([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:7][CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:5]2([CH2:3][OH:2])[CH2:6][CH2:7]2)[CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69960020Methyl 1-(pyridin-3-yl)cyclopropane-1-carboxylate

Product 1

HCID 184089691-(3-Pyridinyl)cyclopropanemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of 7-2 (76 g, 398 mmol) in 500 mL THF was added LiAlH4 (1.0M, 250 mL, 250 mmol) gradually. The reaction mixture was stirred for 2 hr and quenched sequentially with 9.5 mL H2O, 9.5 mL 15% NaOH, and 28.5 mL H2O. The mixture was stirred overnight. Celite (50 g) was added and the mixture stirred for 20 min and filtered through a silica gel plug and concentrated to afford the desired product 7-3 as an oil which was used in the next step without further purification.

Workup

  1. customquenched sequentially with 9.5 mL H2O, 9.5 mL 15% NaOH, and 28.5 mL H2O
  2. stirringThe mixture was stirred overnight
  3. additionCelite (50 g) was added
  4. stirringthe mixture stirred for 20 min
  5. filtrationfiltered through a silica gel plug
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9f7819fa4264dc0937b8638ad328468
Source dataset
uspto-grants-2002_10
Patent number
US06472403B2

Reaction notes

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