Acetyl chloride → HCID 20148603, compound

HRID 569164Notes

Reaction equation

HRID 569164 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][C:7]([C:9]1[CH:21]=[CH:20][C:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)=[O:8].C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30].C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[C:29]([O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][C:7]([C:9]1[CH:21]=[CH:20][C:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)=[O:8])(=[O:31])[CH3:30]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 20148639HCID 20148639, compound

Product 1

HCID 20148603HCID 20148603, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In 30 ml of methylene chloride were dissolved 3.0 g of 3-[p-[3-(2-hydroxyethyl)oxypropionyl]benzyl]pyridine and 1.61 ml of triethylamine, and into the resulting solution was dropped 0.90 ml of acetyl chloride over 30 minutes with ice-cooling. The resulting mixture was subjected to reaction at room temperature for 2 hours, after which 20 ml of water was added to the reaction mixture. The pH of the mixture was adjusted to 7 with sodium hydrogencarbonate, and the organic layer was separated, washed with 10 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: benzene:ethyl acetate (1:1 by volume)] to obtain 2.94 g (yield 85.7%) of pale yellow, oily 3-[p-[3-(2-acetoxyethyl)oxypropionyl]benzyl]pyridine.

Workup

  1. temperaturecooling
  2. customThe resulting mixture was subjected to reaction at room temperature for 2 hours
  3. customthe organic layer was separated
  4. washwashed with 10 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: benzene:ethyl acetate (1:1 by volume)]

Sources & evidence

ORD record
ord-dbadbb690b2b4b45945fd72b0fd348eb
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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