Aluminium lithium hydride → Thieno[3,2-c]pyridin-2-ylmethanol

HRID 1890514Notes

Reaction equation

HRID 1890514 reaction equation
[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[C:10](OC)=[O:11].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22047666Methyl thieno[3,2-c]pyridine-2-carboxylate

Product 1

HCID 46784992Thieno[3,2-c]pyridin-2-ylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl thieno[3,2-c]pyridine-2-carboxylate (D-2) (15 g, 77.6 mmol) in anhydrous THF (250 mL) was added LiAlH4 (4.42 g, 116.4 mmol) in portions at 0° C. The suspension was stirred at 0° C. for 1 h and then quenched by adding saturated aqueous NH4Cl and filtered. The filtrate was washed with brine and concentrated. The residue was used in the next step without any further purification (10.3 g).

Workup

  1. customquenched
  2. additionby adding saturated aqueous NH4Cl
  3. filtrationfiltered
  4. washThe filtrate was washed with brine
  5. concentrationconcentrated
  6. customThe residue was used in the next step without any further purification (10.3 g)

Sources & evidence

ORD record
ord-9a11f58a67a54865a132466060bfcbf4
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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