Water → 2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethanol

HRID 1807059Notes

Reaction equation

HRID 1807059 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][C@H:9]1[C:13]([CH3:15])([CH3:14])[O:12][C:11]([CH3:17])([CH3:16])[O:10]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH3:16][C:11]1([CH3:17])[O:10][C@@H:9]([CH2:8][CH2:7][OH:6])[C:13]([CH3:15])([CH3:14])[O:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67299820tert-butyl-dimethyl-[2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethoxy]-silane

Product 1

HCID 672994832-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step F To the solution of tert-butyl-dimethyl-[2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethoxy]-silane (4.56 g, 15.8 mmol) in tetrahydrofuran (20 mL) at 0° C. was added a solution of tetrabutylammonium fluoride (1 M, 20 mL, 20 mmol). The reaction mixture was stirred at room temperature for 1 h. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated to give 2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethanol as a yellow oil (2.7 g, 100%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa11ba77150a4d23a335711a9a18d4df
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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