Hydrochloric Acid → HCID 54492263, compound

HRID 569176Notes

Reaction equation

HRID 569176 reaction equation
[C:1]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH:11]([C:13]1[CH:25]=[CH:24][C:16]([CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:15][CH:14]=1)O)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.C1CCN2C(=NCCC2)CC1.Cl>C(Cl)Cl.CN(C)C=O.C1(C)C=CC=CC=1.O>[C:1]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH:10]=[CH:11][C:13]1[CH:25]=[CH:24][C:16]([CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:15][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20148617HCID 20148617, compound

Product 1

HCID 54492263HCID 54492263, compoundYield 75%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In 3 ml of methylene chloride was dissolved 630 mg of 3-[p-[3-(2-tert-butoxyethyl)oxy-1-hydroxypropyl]benzyl]pyridine, and to the resulting solution was added 0.27 ml of thionyl chloride with ice-cooling, after which the resulting mixture was subjected to reaction at room temperature for 30 minutes. The solvent and the excessive thionyl chloride were removed by distillation under reduced pressure, and the residue thus obtained was dissolved in 3 ml of N,N-dimethylformamide, and 1.38 ml of DBU was added to the resulting solution, after which the resulting mixture was subjected to reaction at a temperature of 110° to 115° C. for 2 hours. To the reaction mixture were added 10 ml of water and 10 ml of toluene, and the pH of the mixture was adjusted to 7.5 with 2N hydrochloric acid. The organic layer was separated, washed with 5 ml of water, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene:ethyl acetate (10:1 by volume)] to obtain 450 mg (yield 75.0%) of colorless, oily 3-[p-[3-(2-tert-butoxyethyl)oxy-1-propenyl]benzyl]pyridine.

Workup

  1. temperaturecooling
  2. customafter which the resulting mixture was subjected to reaction at room temperature for 30 minutes
  3. customThe solvent and the excessive thionyl chloride were removed by distillation under reduced pressure
  4. customthe residue thus obtained
  5. customafter which the resulting mixture was subjected to reaction at a temperature of 110° to 115° C. for 2 hours
  6. customThe organic layer was separated
  7. washwashed with 5 ml of water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customthe residue thus obtained
  11. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene:ethyl acetate (10:1 by volume)]

Sources & evidence

ORD record
ord-78f3e8a22f2b4b2a98f13bc5971932fe
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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