Tetrahydrofuran → HCID 69967939, compound

HRID 1108895Notes

Reaction equation

HRID 1108895 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C:17](OCC)=O)[N:11]=1)[CH3:8].C1C[O:25]CC1>>[CH2:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([OH:25])[CH3:17])[N:11]=1)[CH3:8]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 54539135HCID 54539135, compound

Product 1

HCID 69967939HCID 69967939, compound

Conditions

Temperature
0 °C

Procedure

To a mechanically stirred solution of LiAlH4 in THF(1.0 M, 20 mL, 20.4 mmol) was added dropwise a solution of ethyl 2-(ethylamino)-6-pyridylacetate (1 g, 4.1 mmol) in THF (30 mL). After the addition was completed, the reaction mixture was heated to reflux. After 5 hr, the reaction was cooled to 0° C. and quenched with 10% NaOH solution. The solids were removed by filtration, and the filtrate was concentrated in vacuum. The residue was dissolved in CH2Cl2, and the solution was dried (MgSO4) and concentrated. Reconcentration from toluene (3 x) gave the title compound as a colorless oil: MS (ES) 167 (M+H)+.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated to reflux
  3. customquenched with 10% NaOH solution
  4. customThe solids were removed by filtration
  5. concentrationthe filtrate was concentrated in vacuum
  6. dissolutionThe residue was dissolved in CH2Cl2
  7. dry with materialthe solution was dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cf64bb4b23ae4bef9eef92fff0305ff4
Source dataset
uspto-grants-2000_05
Patent number
US06069158

Reaction notes

Loading…