Tetrabutylammonium Fluoride → HCID 90025638, compound

HRID 1506966Notes

Reaction equation

HRID 1506966 reaction equation
[CH2:1]([C@@H:8]1[O:12][C:11]([CH3:14])([CH3:13])[O:10][C@H:9]1[CH2:15][CH2:16][O:17][Si](C(C)(C)C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[CH2:1]([C@@H:8]1[O:12][C:11]([CH3:14])([CH3:13])[O:10][C@H:9]1[CH2:15][CH2:16][OH:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90026852HCID 90026852, compound

Product 1

HCID 90025638HCID 90025638, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2-((4S,5S)-5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy)(tert-butyl)dimethylsilane (Preparation example 240, 11.5 g, 32.80 mmol) in THF (115 mL) was slowly added tetrabutylammonium fluoride (TBAF, 1.0M in THF, 48.8 mL, 48.8 mmol) at room temperature. The mixture was stirred for 5 h. The resulting mixture was diluted with EtOAc, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated. The crude compound was purified by a silica gel column to produce the title compound (7.3 g, 80˜95%)

Workup

  1. customat room temperature
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-8451e6cd063447dd9487c7345af80178
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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