Triethylamine → HCID 12973079, compound

HRID 2229236Notes

Reaction equation

HRID 2229236 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]([C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[CH:12]=2)O)[CH:2]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[CH:12]1[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[CH:19]=[CH:20][C:11]=1/[CH:9]=[CH:8]/[CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1.[CH:12]1[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[CH:19]=[CH:20][C:11]=1/[CH:9]=[CH:8]\[CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18467038HCID 18467038, compound

Product 2

HCID 12973079HCID 12973079, compoundHCID 59901126HCID 59901126, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 3-(3-pyridyl)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)propanol (2.29 g) in CH2Cl2 (50 ml) were added triethylamine (2.4 ml) and methanesulfonyl chloride (0.86 ml ). The mixture was stirred at room temperature for 16 hours. The mixture was washed with water and brine, dried and concentrated. The residue was mixed with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.59 g) and stirred at 100° C. for 45 minutes. 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)-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-propen-1-yl]pyridine (216 mg) and 3-[(Z)-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-propen-1-yl]pyridine (245 mg). 3-[(E)-(5,6,7,8-Tetrahydronaphthalen-2-yl)-2-propen-1-yl]pyridine

Workup

  1. washThe mixture was washed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. additionThe residue was mixed with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.59 g)
  5. stirringstirred at 100° C. for 45 minutes
  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-1ee9eec433a1405bbb080d3c19656fd4
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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