Acetone → HCID 19088079, compound

HRID 1646826Notes

Reaction equation

HRID 1646826 reaction equation
[N:1]1([C:6]2[CH:22]=[CH:21][C:9]([C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.B.[Na].CC(C)=O>CO>[OH:11][CH:10]([C:9]1[CH:8]=[CH:7][C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:22][CH:21]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 180AcetoneHCID 19088047HCID 19088047, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 19088079HCID 19088079, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (90 ml) was dissolved 9.00 g (30 mmole) methyl 6-[4-(1-imidazolyl)benzoyl]hexanoate, and the solution was stirred under ice-cooling. 0.86 Gram (30×0.75 mmole) of of sodium boron hydride was added to it, and stirring was continued for 30 minutes under ice-cooling. After acetone was added, the solvent was distilled off, and chloroform and water were added to the residue to effect extraction. The chloroform layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated to give 9.10 g (100%) of methyl 7-hydroxy-7-[4-(1-imidazolyl)phenyl]heptanoate (part of the compound was recrystallized from ethyl acetate/isopropyl ether. m.p. 77°-78° C.).

Workup

  1. temperaturecooling
  2. stirringstirring
  3. temperaturecooling
  4. distillationthe solvent was distilled off
  5. additionchloroform and water were added to the residue
  6. extractionextraction
  7. customThe chloroform layer was separated out
  8. washwashed with aqueous sodium chloride solution
  9. dry with materialdried (magnesium sulfate)
  10. customevaporated

Sources & evidence

ORD record
ord-2665a4ab412a4283a00d2b6c73d106f2
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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