Acetone → HCID 10478752, compound

HRID 2396514Notes

Reaction equation

HRID 2396514 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:31][C:32]([CH3:34])=O.[BH4-].[Na+]>C(O)(=O)C.O>[CH:32]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:9]=2)=[CH:4][CH:3]=1)([CH3:34])[CH3:31]

Participants

6

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 10431342HCID 10431342, compound

Product 1

HCID 10478752HCID 10478752, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 6-{[4-(4-aminophenyl)-6-phenyl-2-pyridyl]oxy}hexanoate (3 g) and acetone (0.54 cc) in acetic acid (45 cc), brought to 15° C., is slowly added sodium borohydride (1.14 g) so as to maintain the temperature below 22° C. The mixture is then stirred at room temperature for 4 hours. The reaction mixture is then poured in distilled water (150 cc) and extracted with ethyl ether (2×100 cc). The combined organic phases are washed with distilled water until neutrality, dried over sodium sulphate and concentrated to dryness at 40° C. under reduced pressure. The oily residue obtained is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 9-1 as a yellow oil).

Workup

  1. custombrought to 15° C.
  2. temperatureto maintain the temperature below 22° C
  3. extractionextracted with ethyl ether (2×100 cc)
  4. washThe combined organic phases are washed with distilled water until neutrality
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness at 40° C. under reduced pressure
  7. customThe oily residue obtained
  8. customis purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 9-1 as a yellow oil)

Sources & evidence

ORD record
ord-01708e4e3bdc414ea7526c36defd0513
Source dataset
uspto-grants-1996_02
Patent number
US05492915

Reaction notes

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