Water → 3-[p-[3-(2-Hydroxyethyl)oxy-2-methyl-1-propenyl]benzyl]pyridine

HRID 569175Notes

Reaction equation

HRID 569175 reaction equation
Cl[CH:2]([C:10]1[CH:22]=[CH:21][C:13]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:12][CH:11]=1)[CH:3]([CH3:9])[CH2:4][O:5][CH2:6][CH2:7][OH:8].C1CCN2C(=NCCC2)CC1.O>CS(C)=O>[OH:8][CH2:7][CH2:6][O:5][CH2:4][C:3]([CH3:9])=[CH:2][C:10]1[CH:22]=[CH:21][C:13]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137455253-[p-[1-Chloro-3-(2-hydroxyethyl)oxy-2-methylpropyl]benzyl]pyridine

Product 1

HCID 536849613-[p-[3-(2-Hydroxyethyl)oxy-2-methyl-1-propenyl]benzyl]pyridineYield 62%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 29.1 ml of dimethylsulfoxide was dissolved 5.82 g of 3-[p-[1-chloro-3-(2-hydroxyethyl)oxy-2-methylpropyl]benzyl]pyridine, and 5.44 ml of DBU was added to the resulting solution, after which the resulting mixture was subjected to reaction at a temperature of 100° to 110° C. for 2 hours. The reaction mixture was poured into 200 ml of water, and the resulting mixture was subjected to extraction with two 50-ml portions of ethyl acetate. The extracts were combined, washed with 20 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: chloroform] to obtain 3.20 g (yield 62.0%) of colorless, oily 3-[p-[3-(2-hydroxyethyl)oxy-2-methyl-1-propenyl]benzyl]pyridine.

Workup

  1. additionwas added to the resulting solution
  2. customafter which the resulting mixture was subjected to reaction at a temperature of 100° to 110° C. for 2 hours
  3. extractionthe resulting mixture was subjected to extraction with two 50-ml portions of ethyl acetate
  4. washwashed with 20 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform]

Sources & evidence

ORD record
ord-be01d6c264ff4cf5a7d265a028a92074
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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