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 1380120Notes

Reaction equation

HRID 1380120 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 6-[2-hydroxy-1-(1H-imidazol-1-yl methyl)ethoxy]hexanoate as a pale yellow oil.

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)

Sources & evidence

ORD record
ord-19c5001fd8fe4d0b96d74eb0a0b4b4b1
Source dataset
uspto-grants-1986_04
Patent number
US04579862

Reaction notes

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