Tetrahydrofuran → 2-Hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzoic acid

HRID 2220603Notes

Reaction equation

HRID 2220603 reaction equation
C([O:8][C:9]1[CH:24]=[C:23]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH:22]=[CH:21][C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])C1C=CC=CC=1.O1CCCC1>CO.[C].[Pd]>[OH:8][C:9]1[CH:24]=[C:23]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH:22]=[CH:21][C:10]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 23090759Benzyl 2-benzyloxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 231343212-Hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzoic acidYield 101.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 2-benzyloxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.243 g) in methanol (6 mL)/tetrahydrofuran (6 mL) was added 10% palladium-carbon (0.05 g) at room temperature under an atmosphere of argon. The mixture was stirred at room temperature for 3 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 (0.146 g).

Workup

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

Sources & evidence

ORD record
ord-01243eb9410245c1b7a5803f6f624f86
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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