Ethyl 5-(2-phenyleth-1-ynyl)nicotinate → (E)-(5-Styrylpyridin-3-yl)-methanol

HRID 606942Notes

Reaction equation

HRID 606942 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[N:7][CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:11](/[C:9]1[CH:10]=[C:5]([CH2:4][OH:3])[CH:6]=[N:7][CH:8]=1)=[CH:12]\[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 2779231Ethyl 5-(2-phenyleth-1-ynyl)nicotinateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 67047921(E)-(5-Styrylpyridin-3-yl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of commercially available 5-phenylethynyl-nicotinic acid ethyl ester (0.4 g, 1.59 mmol) in dry tetrahydrofuran (20 mL) to a solution of lithium aluminum hydride (20 mL, 0.08 M in tetrahydrofuran) at room temperature under nitrogen and stir for 3 h. Add a solution of lithium aluminum hydride (2 mL, 1 M in tetrahydrofuran) and stir for 1 h. Slowly add methanol (2 mL) and concentrate. Dilute with ethyl acetate, wash with water and a saturated aqueous solution of sodium chloride and dry. Purify the residue by silica gel chromatography, eluting with 5:1 hexanes:ethyl acetate to 10:90 hexanes:ethyl acetate, to give the E-isomer (7 mg, 2%).

Workup

  1. stirringstir for 1 h
  2. concentrationSlowly add methanol (2 mL) and concentrate
  3. additionDilute with ethyl acetate
  4. washwash with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dry
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 5:1 hexanes
  8. customethyl acetate to 10:90 hexanes:ethyl acetate, to give the E-isomer (7 mg, 2%)

Sources & evidence

ORD record
ord-884ac9bbc70846c6bf63329f3c45c4f2
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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