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

HRID 1475737Notes

Reaction equation

HRID 1475737 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 8028TetrahydrofuranSolvent

Procedure

9.0 g of tert-butyl-dimethyl-[2-(3-oxetan-3-yl-phenyl)-ethoxy]-silane and 92.3 ml of a 1 N solution of tetra-n-butylammonium fluoride were dissolved in 200 ml of anhydrous THF. The mixture was stirred for 3 h at room temperature. Then the mixture was poured into 200 ml of a saturated aqueous solution of sodium hydrogencarbonate and extracted three times with 500 ml each of EA The combined organic layers were dried with magnesium sulfate and evaporated. The residue was purified by silica gel chromatography (HEP/EA gradient) to yield 4.9 g of the title compound.

Workup

  1. extractionextracted three times with 500 ml each of EA The combined organic layers
  2. dry with materialwere dried with magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-284105bb8a8748bba0887f7ad0bbde6c
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

Loading…