Ethylene Glycol → 1-(Pyrid-3-yl)-2-(2-bromophenyl)-ethanediol

HRID 1613639Notes

Reaction equation

HRID 1613639 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=[O:17])[CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Br:16])O)[CH:2]=1.[BH4-].[Na+].Cl.C(O)C[OH:23]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:17])([OH:23])[CH2:8][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Br:16])[CH:2]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 197741961-(Pyrid-3-yl)-2-(2-bromophenyl)-2-hydroxyethanone

Product 1

HCID 197741971-(Pyrid-3-yl)-2-(2-bromophenyl)-ethanediol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 g (0.068 mol) of 1-(pyrid-3-yl)-2-(2-bromophenyl)-2-hydroxyethanone in 300 ml of methanol were reduced with 3 g (0.079 mol) of sodium borohydride at 0° C. Stirring was carried out for a few hours at room temperature (21° C.), the pH was brought to 2 with 4N hydrochloric acid and 4 ml of ethylene glycol were added. The solution was evaporated down, after which the residue was covered with a layer of ethyl acetate and neutralized with NaHCO3 solution. The ethyl acetate phase was washed twice with water and dried over Na2SO4. After the ethyl acetate had been distilled off, the product was obtained as a white powder of melting point 115° C.

Workup

  1. waitwas carried out for a few hours at room temperature
  2. custom(21° C.)
  3. additionwere added
  4. customThe solution was evaporated down
  5. washThe ethyl acetate phase was washed twice with water
  6. dry with materialdried over Na2SO4
  7. distillationAfter the ethyl acetate had been distilled off
  8. customthe product was obtained as a white powder of melting point 115° C.

Sources & evidence

ORD record
ord-bcdbc5e5795b45fca221e53df83d02ea
Source dataset
uspto-grants-1993_03
Patent number
US05194441

Reaction notes

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