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

HRID 1198523Notes

Reaction equation

HRID 1198523 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 aluminium hydride (0.25 g) was 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 was stirred for 30 minutes, diluted with sodium hydroxide solution and extracted with ethyl acetate. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:1).

Workup

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

Sources & evidence

ORD record
ord-8c1737dd31744314bfac3358eb33d22e
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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