Sodium Bicarbonate → 2-(3-Oxetan-3-yl-phenyl)-ethanol

HRID 1918381Notes

Reaction equation

HRID 1918381 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]2[CH2:18][O:17][CH2:16]2)[CH:10]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[O:17]1[CH2:18][CH:15]([C:11]2[CH:10]=[C:9]([CH2:8][CH2:7][OH:6])[CH:14]=[CH:13][CH:12]=2)[CH2:16]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 67170174tert-Butyl-dimethyl-[2-(3-oxetan-3-yl-phenyl)-ethoxy]-silane

Product 1

HCID 671700292-(3-Oxetan-3-yl-phenyl)-ethanolYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

9.0 g of tert-Butyl-dimethyl-[2-(3-oxetan-3-yl-phenyl)-ethoxy]-silane were dissolved using 200 ml of anhydrous THF and 92 ml of a 1M solution of tetra-n-butylammonium fluoride in THF added at room temperature. The reaction mixture was stirred at room temperature for 3 h and then poured into 500 ml of a saturated aqueous NaHCO3-solution and extracted three times using 300 ml of EA each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP (gradient) yielded 4.9 g of the title compound, colorless oil.

Workup

  1. additionadded at room temperature
  2. extractionextracted three times
  3. customThe organic layer was then dried
  4. customevaporated

Sources & evidence

ORD record
ord-90e7fd58603649119ce7489e4a9be1f4
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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