Sodium periodate → [4-(2-{[Tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylpropoxy)phenyl]boronic acid

HRID 1674304Notes

Reaction equation

HRID 1674304 reaction equation
[C:1]([Si:5]([O:8][CH:9]([CH3:29])[C:10]([CH3:28])([O:12][C:13]1[CH:18]=[CH:17][C:16]([B:19]2[O:23]C(C)(C)C(C)(C)[O:20]2)=[CH:15][CH:14]=1)[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+]>Cl.O1CCCC1.O>[Si:5]([O:8][CH:9]([CH3:29])[C:10]([CH3:28])([CH3:11])[O:12][C:13]1[CH:18]=[CH:17][C:16]([B:19]([OH:20])[OH:23])=[CH:15][CH:14]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 57460957tert-Butyl{1,2-dimethyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propoxy}dimethylsilane

Product 1

HCID 57460958[4-(2-{[Tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylpropoxy)phenyl]boronic acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl{1,2-dimethyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propoxy}dimethylsilane (5.8 g) was dissolved in 1 M hydrochloric acid (20 mL)-tetrahydrofuran (20 mL)-water (20 mL), sodium periodate (5.9 g) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the title compound as a pale-yellow solid (1.1 g, 23%).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washwashed with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9f4612dbadf24a0f8e88bca84df93c4d
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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