Water → HCID 18182429, compound

HRID 1359327Notes

Reaction equation

HRID 1359327 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH2:7]([C:14]1[C:19]([O:20][CH2:21][O:22][CH3:23])=[CH:18][CH:17]=[C:16]([CH2:24][CH2:25][C:26](OCC)=[O:27])[N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>CCOCC>[CH2:7]([C:14]1[C:19]([O:20][CH2:21][O:22][CH3:23])=[CH:18][CH:17]=[C:16]([CH2:24][CH2:25][CH2:26][OH:27])[N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18182193HCID 18182193, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18182429HCID 18182429, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

205 mg of aluminum lithium hydride was suspended in 20 ml of anhydrous ether. A solution of 10 ml of anhydrous ether containing 1.3 g of 2-benzyl-6-(2-ethoxycarbonylethyl)-3-methoxymethyloxypyridine was added dropwise under ice-cooling. After stirring for one hour as it was, 0.2 ml of water, then 0.2 ml of an aqueous 5N sodium hydroxide solution and then 0.6 ml of water were added thereto under ice-cooling. The reaction solution was filtered through filter paper to remove insoluble matters. After washing with ether, the organic phase was evaporated. The residue was subjected to silica gel column chromatography using 40% ethyl acetate/hexane as an eluent for separation and purification, to give 1.0 g of the target compound.

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. filtrationThe reaction solution was filtered
  4. filtrationthrough filter paper
  5. customto remove insoluble matters
  6. washAfter washing with ether
  7. customthe organic phase was evaporated
  8. customfor separation and purification

Sources & evidence

ORD record
ord-5c08378b2b6c44dbaa35db14490754ad
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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