Aluminium lithium hydride → HCID 58636747, compound

HRID 1158984Notes

Reaction equation

HRID 1158984 reaction equation
C[O:2][C:3]([C:5]1[C:6]([CH:17]2[CH2:19][CH2:18]2)=[N:7][C:8]([CH3:16])=[C:9]([OH:15])[C:10]=1[C:11](OC)=[O:12])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH:17]1([C:6]2[N:7]=[C:8]([CH3:16])[C:9]([OH:15])=[C:10]([CH2:11][OH:12])[C:5]=2[CH2:3][OH:2])[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58636771HCID 58636771, compound

Product 1

HCID 58636747HCID 58636747, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 2-cyclopropyl-5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid dimethyl ester (165) (30 g, 113 mmol) in anhydrous tetrahydrofuran (400 mL) was slowly cannulated into a suspension of LiAlH4 in anhydrous tetrahydrofuran (400 mL) at 0° C. The reaction mixture was heated at 60° C. for 3 hours, cooled in an ice bath and slowly quenched with water. The colorless gel formed was filtered off through a celite pad and washed with methyl alcohol. The filtrate was evaporated to dryness to give 6-cyclopropyl-4,5-bis-hydroxymethyl-2-methyl-pyridin-3-ol (166) (15.0 g, 63% yield) as a colorless solids.

Workup

  1. temperaturecooled in an ice bath
  2. customslowly quenched with water
  3. customThe colorless gel formed
  4. filtrationwas filtered off through a celite pad
  5. washwashed with methyl alcohol
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-a2b032b2b54c43c4bfc581b8d775966a
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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