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

HRID 1475736Notes

Reaction equation

HRID 1475736 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+]>C(O)(C)C.[Ni](I)I.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

8

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]-silane

Reagents, catalysts & solvents 3

HCID 26038Nickel(II) iodideCatalystHCID 735777(1R,2R)-2-AminocyclohexanolCatalystHCID 3776IsopropanolSolvent2×

Procedure

4.6 g of 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenylboronic acid, 130 mg of nickel iodide, 5.0 g of sodium bis(trimethylsilyl)amide and 62 mg of (1R,2R)-2-aminocyclohexanol were placed in a microwave vial and 3.5 ml of isopropanol were added. The mixture was stirred for 10 min at room temperature. Then a solution of 3-iodooxetane in 1.5 ml of isopropanol was added and the mixture treated under microwave irradiation at 80° C. for 30 min. The obtained mixture was combined with the mixtures obtained in three further runs of the synthesis, poured into 50 ml of a saturated aqueous sodium hydrogencarbonate solution and extracted three time with 50 ml each of EA. The combined organic layers were dried with magnesium sulfate and evaporated to yield 9.0 g of the title compound.

Workup

  1. additionwere added
  2. additionthe mixture treated under microwave irradiation at 80° C. for 30 min
  3. customobtained in three further runs of the synthesis
  4. extractionextracted three time with 50 ml each of EA
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-60e1331a1e364d2aab6a02e7ef27b15f
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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