Water → HCID 13745530, compound

HRID 569180Notes

Reaction equation

HRID 569180 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[C:15](\[CH3:21])/[C:16](OCC)=[O:17])=[CH:10][CH:9]=2)[CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:9]=[CH:10][C:11](/[CH:14]=[C:15](\[CH3:21])/[CH2:16][OH:17])=[CH:12][CH:13]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 12904568HCID 12904568, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13745530HCID 13745530, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 33 ml of anhydrous tetrahydrofuran was dissolved 6.5 g of ethyl (E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylacrylate, and to the resulting solution was added 0.66 g of lithium aluminum hydride in small portions at room temperature. Further, the resulting mixture was subjected to reaction at the same temperature for one hour, and thereafter, 30 ml of ethyl acetate and then 2.5 ml of water were added in small portions with water-cooling. The insolubles were removed by filtration, and thereafter, the organic layer was dried over anhydrous magnesium sulfate. Subsequently, the solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (3:1 by volume)], to obtain 4.0 g (yield 72.3%) of colorless, oily (E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyl alcohol.

Workup

  1. customFurther, the resulting mixture was subjected to reaction at the same temperature for one hour
  2. temperaturecooling
  3. customThe insolubles were removed by filtration
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customSubsequently, the solvent was removed by distillation under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (3:1 by volume)]

Sources & evidence

ORD record
ord-c6da5d5eaa09489cbd6de4b8f954c265
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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