Water → HCID 12368131, compound

HRID 900965Notes

Reaction equation

HRID 900965 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:13]([CH3:24])=[N:14][C:15]([CH3:23])=[C:16]([C:18](OCC)=[O:19])[CH:17]=1)=O)C.O>C(OCC)C>[OH:9][CH2:10][C:12]1[CH:17]=[C:16]([CH2:18][OH:19])[C:15]([CH3:23])=[N:14][C:13]=1[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 245983Diethyl 2,6-dimethylpyridine-3,5-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12368131HCID 12368131, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
40 °C

Procedure

To a ice-cooled mixture of lithium aluminum hydride (95%) (6.7 g, 168 mmol) in anhydrous diethyl ether (750 mL) is added a solution of 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester (31.5 g, 125 mmol) in diethyl ether (250 mL) via cannula under a stream of nitrogen. After the addition is complete, the reaction mixture is warmed to 40° C. for 0.5 h. After cooling to 0° C., water (50 mL) is added slowly under a stream of nitrogen. The resulting solids are filtered, washed with diethyl ether (250 mL), suspended in methanol (700 mL) and warmed to a gentle reflux (1 h). The remaining aluminum salts are filtered hot and washed with hot methanol (200 mL). The filtrate is concentrated and dried in vacuo to afford 5-hydroxymethyl-2,6-dimethyl-pyridin-3-yl-methanol as a white solid and is used in the subsequent step without further purification: Rf 0.16 (10% methanol in chloroform); 1H NMR (DMSO-d6, 300 MHz) δ 7.62 (s, 1 H), 4.45 (s, 4 H), 2.34 (s, 6 H); ESI-LCMS m/z calcd for C9H13NO2: 167.1; found 168.0 (M+1)+.

Workup

  1. additionAfter the addition
  2. temperatureAfter cooling to 0° C.
  3. filtrationThe resulting solids are filtered
  4. washwashed with diethyl ether (250 mL)
  5. temperaturewarmed to
  6. temperaturea gentle reflux (1 h)
  7. filtrationThe remaining aluminum salts are filtered hot
  8. washwashed with hot methanol (200 mL)
  9. concentrationThe filtrate is concentrated
  10. customdried in vacuo

Sources & evidence

ORD record
ord-b32f8249e0784231a13f1843de39e32a
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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