Benzyl [2-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetate → [2-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetic acid

HRID 30750Notes

Reaction equation

HRID 30750 reaction equation
[CH:1]([C:4]1[CH:21]=[C:20]([B:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]2)[CH:19]=[CH:18][C:5]=1[O:6][CH2:7][C:8]([O:10]CC1C=CC=CC=1)=[O:9])([CH3:3])[CH3:2]>C(O)C.[C].[Pd]>[CH:1]([C:4]1[CH:21]=[C:20]([B:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]2)[CH:19]=[CH:18][C:5]=1[O:6][CH2:7][C:8]([OH:10])=[O:9])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86605504Benzyl [2-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetate

Product 1

HCID 23134282[2-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetic acidYield 83.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl [2-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetate (0.24 g) and 10% palladium-carbon (0.05 g) in ethanol (10 mL) was stirred at room temperature for 2 hrs under an atmosphere of hydrogen. The catalyst was removed by filtration, and the solvent was evaporated under reduced pressure to afford the title compound (0.156 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a501d2f600a24a658735bf595c705db3
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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