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

HRID 1990053Notes

Reaction equation

HRID 1990053 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-ef3a6c8668e44a66be22beee8a7d0027
Source dataset
uspto-grants-2010_01
Patent number
US07642263B2

Reaction notes

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