Triethylamine → HCID 12973078, compound

HRID 2229232Notes

Reaction equation

HRID 2229232 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11](O)[CH2:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.CNC1C=CN=CC=1>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]\[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1230984-(Methylamino)pyridineHCID 18467036HCID 18467036, compound

Product 2

HCID 12973078HCID 12973078, compoundHCID 59901125HCID 59901125, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 1-(2-naphthyl)-3-(3-pyridyl)propan-1-ol (1.14 g) in CH2Cl2 (30 ml) were added triethylamine (2.5 ml), methanesulfonyl chloride (0.70 ml) and catalytic amount of 4-methylaminopyridine. The mixture was stirred at room temperature for 8 hours. The mixture was washed with water and brine, dried and concentrated. The residue was dissolved in 1,8-diazabicyclo[5.4.0]undec-7-ene (20 ml) and stirred at 90° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried and concentrated. The residue was chromatographed on silica gel (hexane-ethyl acetate=3:1) to give 3-[(E)-3-(2-naphthyl)-2-propen-1-yl]pyridine (123 mg) and 3-[(Z)-3-(2-naphthyl)-2-propen-1-yl]pyridine (67 mg). 3-[(E)-3-(2-naphthyl)-2-propen-1-yl]pyridine.

Workup

  1. washThe mixture was washed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 1,8-diazabicyclo[5.4.0]undec-7-ene (20 ml)
  5. stirringstirred at 90° C. for 1 hour
  6. additionThe reaction mixture was diluted with ethyl acetate
  7. washwashed with water and brine
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel (hexane-ethyl acetate=3:1)

Sources & evidence

ORD record
ord-1a21508122e74392b8e3069af6d2afef
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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