Methyl 3-(3-(benzyloxy)phenyl)-4-methoxybut-2-enoate → Methyl 3-(3-hydroxyphenyl)-4-methoxybutanoate

HRID 1662580Notes

Reaction equation

HRID 1662580 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH2:21][O:22][CH3:23])=[CH:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:15]([CH2:21][O:22][CH3:23])[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 67428736Methyl 3-(3-(benzyloxy)phenyl)-4-methoxybut-2-enoate

Product 1

HCID 57706204Methyl 3-(3-hydroxyphenyl)-4-methoxybutanoateYield 76.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 102.B (mixture of geometric isomers) (0.11 g, 0.35 mmol) in EtOAc (2 mL) was added Pd/C (10 wt. %) (0.019 g, 0.018 mmol) under N2. The mixture was purged with H2, stirred overnight under a H2 balloon, filtered through silica gel (EtOAc), and concentrated. The crude product was purified by silica gel flash chromatography (10-40% EtOAc/hexane) to afford 102.C (0.060 g, 76%) as a pale yellow oil.

Workup

  1. customThe mixture was purged with H2
  2. filtrationfiltered through silica gel (EtOAc)
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel flash chromatography (10-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-2e950100b36949dbae0eae8dc49346fc
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

Loading…