4-pyridin-3-ylbutanal → HCID 13739739, compound

HRID 1458363Notes

Reaction equation

HRID 1458363 reaction equation
[CH3:1][Mg]Br.[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH2:12][CH:13]=[O:14])[CH:5]=1>O1CCCC1>[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH2:12][CH:13]([OH:14])[CH3:1])[CH:5]=1

Participants

4

Reactant 2

HCID 110190264-pyridin-3-ylbutanalHCID 178418573HCID 178418573, compound

Product 1

HCID 13739739HCID 13739739, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methylmagnesium bromide (0.75 mL of a 3M solution (diethyl ether) in 3.5 mL dry tetrahydrofuran) at 0° C. was added a solution of 4-pyridin-3-yl-butyraldehyde (133 mg in 1 mL tetrahydrofuran) and the mixture at low temperature. After 30 minutes, the reaction was quenched by the addition of saturated ammonium chloride and extracted with ethyl acetate. The organic portion was washed with saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel (methylene chloride:methanol, 95:5) gave the title compound (71 mg).

Workup

  1. customthe reaction was quenched by the addition of saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe organic portion was washed with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-cb9ae2a690194930bc7aa66a189899aa
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

Loading…