6-[2-Imidazol-1-yl-1-(4-methoxy-benzyloxymethyl)-ethoxy]-hexanoic acid ethyl ester → ethyl 6-[2-hydroxy-1-(1H-imidazol-1-yl methyl)ethoxy]hexanoate

HRID 845476Notes

Reaction equation

HRID 845476 reaction equation
[N:1]1([CH2:6][CH:7]([CH2:19][O:20]CC2C=CC(OC)=CC=2)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=[CH:4][N:3]=[CH:2]1.[H][H]>C(O)C.FC(F)(F)C(O)=O.[Pd]>[OH:20][CH2:19][CH:7]([CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 2

HCID 139048066-[2-Imidazol-1-yl-1-(4-methoxy-benzyloxymethyl)-ethoxy]-hexanoic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 20131189ethyl 6-[2-hydroxy-1-(1H-imidazol-1-yl methyl)ethoxy]hexanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoate (Example 4; 5.8 g 0.014 mol) in ethanol (20 ml) and trifluoroacetic acid (1 ml) containing a catalytic amount of 10% palladium on carbon (0.5 g) was stirred at room temperature under a hydrogen atmosphere. When hydrogen uptake had ceased the solution was filtered and the solvent was evaporated off under reduced pressure. The residue was treated with a saturated aqueous solution of sodium hydrogen carbonate and extracted with dichloromethane. The extracts were dried (Na2SO4) and the solvent was evaporated off under reduced pressure to give the crude product which was purified by column chromatography (silica gel, chloroform to 5% ethanol in chloroform) to give ethyl

Workup

  1. filtrationwas filtered
  2. customthe solvent was evaporated off under reduced pressure
  3. additionThe residue was treated with a saturated aqueous solution of sodium hydrogen carbonate
  4. extractionextracted with dichloromethane
  5. dry with materialThe extracts were dried (Na2SO4)
  6. customthe solvent was evaporated off under reduced pressure
  7. customto give the crude product which
  8. customwas purified by column chromatography (silica gel, chloroform to 5% ethanol in chloroform)
  9. customto give ethyl

Sources & evidence

ORD record
ord-d929d3f76d6643e3800611245bbb8d47
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

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