Benzyl Alcohol → Benzyl 2-pyridin-4-ylacetate

HRID 30391Notes

Reaction equation

HRID 30391 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:3][CH:2]=1.C(O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([Li])CCC>O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10][CH2:11][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 122482Methyl 4-pyridylacetateHCID 178418339Butyllithium

Product 1

HCID 11413519Benzyl 2-pyridin-4-ylacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-pyridylacetate (Step A, 2.5 g, 16 mmol) and benzyl alcohol (3.4 mL, 33 mmol) in anhydrous tetrahydrofuran (10 mL) at −10° C. was added butyllithium (2 M in cyclohexane, 16 mL, 33 mL), and the reaction was allowed to warm to room temperature overnight. The volatile materials were removed on a rotary evaporator, and the residue was diluted with methylene chloride (50 mL), washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to dryness, and the residue was purified by flash column chromatography eluted with 30% ethyl acetate in hexane to give the title compound. 1H NMR (400 MHz, CD3OD): δ 8.43 (d, 2H), 7.38 (d, 2H), 7.32 (m, 5 H), 5.16 (s, 2H), 3.99 (s, 2H).

Workup

  1. customThe volatile materials were removed on a rotary evaporator
  2. additionthe residue was diluted with methylene chloride (50 mL)
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customthe residue was purified by flash column chromatography
  8. washeluted with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1893498573ec4d738f75ba3a3a75f0f1
Source dataset
uspto-grants-2008_09
Patent number
US07423067B2

Reaction notes

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