methyl 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoate → Methyl 3-hydroxy-5-{[(1R)-1-methyl-2-(methyloxy)ethyl]oxy}benzoate

HRID 1176004Notes

Reaction equation

HRID 1176004 reaction equation
[CH3:1][C@@H:2]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17]CC2C=CC=CC=2)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])[CH2:3][O:4][CH3:5]>C1COCC1.C(O)C.[Pd]>[OH:17][C:15]1[CH:14]=[C:9]([CH:8]=[C:7]([O:6][C@H:2]([CH3:1])[CH2:3][O:4][CH3:5])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 1

HCID 59127090methyl 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoate

Product 1

HCID 59127121Methyl 3-hydroxy-5-{[(1R)-1-methyl-2-(methyloxy)ethyl]oxy}benzoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-{[(1R)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(phenylmethyl)oxy]benzoate in THF (5 mL) and ethanol (5 mL), containing 10% palladium on carbon, was stirred under an atmosphere of hydrogen for 16 hours. The palladium on carbon was removed by filtration and the filtrate evaporated under reduced pressure to give the desired material as a clear gum (723 mg).

Workup

  1. customThe palladium on carbon was removed by filtration
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-bc8ec2aff13f4116b18b66ee3babade0
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

Loading…