Hydrochloric Acid → HCID 20148669, compound

HRID 569165Notes

Reaction equation

HRID 569165 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]([C:12]1[CH:24]=[CH:23][C:15]([CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][CH:13]=1)=[O:11])(=[O:3])[CH3:2].B.[Na].O.Cl>C(O)C.C(OCC)(=O)C>[C:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH:10]([C:12]1[CH:24]=[CH:23][C:15]([CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][CH:13]=1)[OH:11])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 20148603HCID 20148603, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 20148669HCID 20148669, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 27 ml of ethanol was dissolved 2.70 g of 3-[p-[3-(2-acetoxyethyl)oxypropionyl]benzyl]pyridine, and to the resulting solution was added 0.34 g of sodium boron hydride in portions with ice-cooling over 30 minutes, after which the resulting mixture was subjected to reaction at the same temperature for one hour. To the reaction mixture were added 30 ml of iced water and 20 ml of ethyl acetate, and then, the pH thereof was adjusted to 2.0 with 2N hydrochloric acid. The aqueous layer was separated, and 30 ml of ethyl acetate was added thereto, after which the pH thereof was adjusted to 7 with sodium hydrogencarbonate. The organic layer was separated, washed with 10 ml of water, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation to obtain 2.25 g (yield 82.7%) of colorless, oily 3-[p-[3-(2-acetoxyethyl)oxy-1-hydroxypropyl]benzyl]pyridine.

Workup

  1. temperaturecooling over 30 minutes
  2. customafter which the resulting mixture was subjected to reaction at the same temperature for one hour
  3. customThe aqueous layer was separated
  4. addition30 ml of ethyl acetate was added
  5. customThe organic layer was separated
  6. washwashed with 10 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-53f35dbd55914f3dbd232853d646e693
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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