Sodium Bicarbonate → tert-Butyl-dimethyl-[2-(3-oxetan-3-yl-phenyl)-ethoxy]-silane

HRID 1475792Notes

Reaction equation

HRID 1475792 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].I[CH:31]1[CH2:34][O:33][CH2:32]1.C([O-])(O)=O.[Na+]>CC(O)C.Cl.N[C@@H]1CCCC[C@H]1O>[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:31]2[CH2:34][O:33][CH2:32]2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 133566863-IodooxetaneHCID 588451363-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-benzeneboronic Acid

Product 1

HCID 67170174tert-Butyl-dimethyl-[2-(3-oxetan-3-yl-phenyl)-ethoxy]-silaneYield 138.4%

Reagents, catalysts & solvents 2

HCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-CatalystHCID 3776IsopropanolSolvent2×

Procedure

18.3 g of 3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-benzeneboronic acid, 510 mg of NiI2, 19.9 g of sodium bis(trimethylsilyl)amide, and 250 mg of trans-2-aminocyclohexanol hydrochloride were added to 14.0 ml of 2-propanol and the mixture was stirred for 10 minutes at room temperature. Then, a solution of 10.0 g of 3-Iodo-oxetane in 6.0 ml of 2-propanol was added and the reaction mixture kept at 80° C. under microwave irradiation for 30 minutes. The reaction mixture was then poured into 100 ml of a saturated aqueous NaHCO3-solution and extracted three times using 100 ml of EA each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP (gradient) yielded 22.0 g of the title compound, colorless oil.

Workup

  1. customthe reaction mixture kept at 80° C. under microwave irradiation for 30 minutes
  2. extractionextracted three times
  3. customThe organic layer was then dried
  4. customevaporated

Sources & evidence

ORD record
ord-e5995b5353e944bdb95790ade43e08df
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

Loading…