HCID 57707135, compound → HCID 57706501, compound

HRID 1662584Notes

Reaction equation

HRID 1662584 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16]CC2C=CC=CC=2)[CH:11]=1)([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5]>CO.[Pd]>[OH:16][C:12]1[CH:11]=[C:10]([C:2]([CH3:1])([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 57707135HCID 57707135, compound

Product 1

HCID 57706501HCID 57706501, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a solution of methyl 3-(3-(benzyloxy)phenyl)-3-methylpentanoate 103.E (100 mg, 320 μmol) in MeOH (5 mL) was added palladium on carbon (34.1 mg, 320 μmol). The reaction was charged with H2 to 50 psi and stirred for 3 hours. The reaction was then filtered through Celite, washed with DCM, stripped, and purified by silica gel chromatography to afford methyl 3-(3-hydroxyphenyl)-3-methylpentanoate 103.F (65.3 mg, 91.8% yield).

Workup

  1. additionThe reaction was charged with H2 to 50 psi
  2. filtrationThe reaction was then filtered through Celite
  3. washwashed with DCM
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-60446554a9354e8eb28c442a1473ff3d
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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