Water → HCID 57460875, compound

HRID 1674230Notes

Reaction equation

HRID 1674230 reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]([CH3:26])([O:10][C:11]1[CH:16]=[CH:15][C:14]([B:17]2[O:21]C(C)(C)C(C)(C)[O:18]2)=[CH:13][CH:12]=1)[CH3:9])(C)(C)C.[O:29]1CC[CH2:31][CH2:30]1.O>C(O)(=O)C.C1(C)C=CC=CC=1>[C:30]([O:6][CH2:7][C:8]([CH3:9])([CH3:26])[O:10][C:11]1[CH:12]=[CH:13][C:14]([B:17]([OH:18])[OH:21])=[CH:15][CH:16]=1)(=[O:29])[CH3:31]

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 57460874HCID 57460874, compound

Product 1

HCID 57460875HCID 57460875, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

A solution of tert-butyl(dimethyl){2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propoxy}silane (5.0 g) in acetic acid (30 mL)-tetrahydrofuran (10 mL)-water (10 mL) was stirred for 2 days. The reaction mixture was diluted with toluene and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane (20 mL), pyridine (2.4 mL), acetic anhydride (1.5 g) and N,N-dimethyl-4-aminopyridine (0.1 g) were added and the mixture was stirred for 2 hr. Small pieces of ice were added to the reaction mixture, and the mixture was stirred for 30 min, 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. The residue was dissolved in 1 M hydrochloric acid (10 mL)-tetrahydrofuran (10 mL)-water (10 mL), sodium periodate (3.2 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. The residue was triturated with diisopropyl ether to give the title compound as a pale-yellow solid (1.6 g, 52%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 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
  6. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  7. additionpyridine (2.4 mL), acetic anhydride (1.5 g) and N,N-dimethyl-4-aminopyridine (0.1 g) were added
  8. additionSmall pieces of ice were added to the reaction mixture
  9. stirringthe mixture was stirred for 30 min
  10. extractionextracted with ethyl acetate
  11. washwashed with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was evaporated under reduced pressure
  14. dissolutionThe residue was dissolved in 1 M hydrochloric acid (10 mL)-tetrahydrofuran (10 mL)-water (10 mL), sodium periodate (3.2 g)
  15. additionwas added
  16. stirringthe mixture was stirred at room temperature for 3 hr
  17. additionThe reaction mixture was diluted with water
  18. extractionextracted with ethyl acetate
  19. washwashed with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  20. dry with materialdried over anhydrous sodium sulfate
  21. customThe solvent was evaporated under reduced pressure
  22. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-889e1b9eb34245389262a03de7b7c1cc
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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