Tetrabutylammonium Fluoride → N-(2-(1,3-Dioxolan-2-yl)ethyl)-N-(2-hydroxyethyl)acetamide

HRID 874822Notes

Reaction equation

HRID 874822 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][N:8]([CH2:12][CH2:13][O:14][Si](C(C)(C)C)(C)C)[C:9](=[O:11])[CH3:10].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][N:8]([CH2:12][CH2:13][OH:14])[C:9](=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86722312HCID 86722312, compound

Product 1

HCID 86722313N-(2-(1,3-Dioxolan-2-yl)ethyl)-N-(2-hydroxyethyl)acetamideYield 69.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(2-(1,3-dioxolan-2-yl)ethyl)-N-(2-((tert-butyldimethylsilyl)oxy)ethyl)acetamide (0.65 g, 2.04 mmol) in THF (5 mL) was added a solution of tetrabutylammonium fluoride (1.0 M in THF, 2.24 mL). The reaction mixture was stirred at RT for 18 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was purified by flash column chromatography eluting with 0 to 100% ethyl acetate/iso-hexane to afford the title compound (0.287 g, 69%) which was used directly in the next step.

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  3. filtrationfiltered
  4. customthe solvent evaporated at reduced pressure
  5. customThe residue was purified by flash column chromatography
  6. washeluting with 0 to 100% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-7004f7719dfb47b8801bbeb4287a3607
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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