Methyl 3-[2(E)-(quinolin-2-yl)ethenyl]benzoate → 3-[2(E)-(Quinolin-2-yl)ethenyl]benzyl alcohol

HRID 54528Notes

Reaction equation

HRID 54528 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1/[CH:17]=[CH:18]/[C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22](OC)=[O:23]>O1CCCC1.[OH-].[Na+]>[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1/[CH:17]=[CH:18]/[C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[CH2:22][OH:23]

Participants

5

Reactant 2

HCID 19959111Methyl 3-[2(E)-(quinolin-2-yl)ethenyl]benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 701100023-[2(E)-(Quinolin-2-yl)ethenyl]benzyl alcohol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Solid lithium aluminum hydride (025 g) is added in portions to a stirred solution of methyl 3-[2(E)-(quinolin-2-yl)ethenyl]benzoate (2.1 g, 7.3 mmol) in tetrahydrofuran (50 ml). The mixture is stirred for 30 minutes, diluted with sodium hydroxide solution and extracted with ethyl acetate. The extract is dried and evaporated and the residue chromatographed on silica in ethyl acetate-hexane.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract is dried
  3. customevaporated
  4. customthe residue chromatographed on silica in ethyl acetate-hexane

Sources & evidence

ORD record
ord-a1c3592617c64a65bc0bbf2a904ca44e
Source dataset
uspto-grants-1997_04
Patent number
US05622969

Reaction notes

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