HCID 20605638, compound → HCID 22318750, compound

HRID 497424Notes

Reaction equation

HRID 497424 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[CH:11]([O:14][CH3:15])[O:12][CH3:13])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:13][O:12][CH:11]([O:14][CH3:15])[C:6]1[C:5]([CH2:4][OH:3])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 20605638HCID 20605638, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 22318750HCID 22318750, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 11.3 g (0.05 mol) of 2-dimethoxymethyl-nicotinic acid ethyl ester dissolved in 150 mL of ether and 2.09 g (0.055 mol) of lithium aluminum hydride is stirred at room temperature for 18 hours. An additional 530 mg of lithium aluminum hydride is added and the reaction mixture stirred for another 3 hours. The reaction mixture is cooled using an ice bath and quenched with 6 mL of 1N NaOH and 8 g of sodium sulfate decahydrate. After a ½ hour the reaction mixture is filtered and the filtrate evaporated. The residue is chromatographed on 180 g of silica gel using ethyl acetate as the eluant. Appropriate fractions are combined and evaporated to yield 4.45 g of (2-dimethoxymethyl-pyridin-3-yl)methanol. 1H NMR (CDCl3) δ 8.40 (d, 1H), 7.70 (d, 1H), 7.20 (m, 1H), 5.35 (s, 1H), 4.75 (s, 2H), 3.40 (s, 3H). Step 4:

Workup

  1. temperatureThe reaction mixture is cooled
  2. customquenched with 6 mL of 1N NaOH and 8 g of sodium sulfate decahydrate
  3. filtrationAfter a ½ hour the reaction mixture is filtered
  4. customthe filtrate evaporated
  5. customThe residue is chromatographed on 180 g of silica gel
  6. customevaporated

Sources & evidence

ORD record
ord-268a65654aab4f628a23b068c4a3f2d4
Source dataset
uspto-grants-2005_09
Patent number
US06949562B2

Reaction notes

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