Methanol → HCID 57707135, compound

HRID 1662583Notes

Reaction equation

HRID 1662583 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=1)([CH2:7][CH3:8])[CH2:3][C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:28]O>>[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=1)([CH2:7][CH3:8])[CH2:3][C:4]([O:6][CH3:28])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 57705599HCID 57705599, compound

Product 1

HCID 57707135HCID 57707135, compoundYield 91.9%

Conditions

Temperature
60 °C

Procedure

Into a solution of 3-(3-(benzyloxy)phenyl)-3-methylpentanoic acid 103.D (184 mg, 617 μmol) in MeOH (3 mL) was injected H2SO4 (3.29 μL, 61.7 μmol), and the mixture was heated at 60° C. overnight. The reaction was quenched with saturated NaHCO3 solution, extracted with DCM, dried over Na2SO4, filtered, stripped, and purified by silica gel chromatography to afford methyl 3-(3-(benzyloxy)phenyl)-3-methylpentanoate 103.E (177 mg, 91.9% yield).

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution
  2. extractionextracted with DCM
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-cd638bca17254af1a6c1f30af78af099
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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