Ammonium Chloride → (R)-1-(tert-butyldimethylsilanyloxy)-3-buten-2-ol

HRID 217974Notes

Reaction equation

HRID 217974 reaction equation
[CH2:1]([Li])CCC.[I-].C[S+](C)C.[CH2:11]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C@@H:12]1[O:14][CH2:13]1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[Si:16]([O:15][CH2:11][C@H:12]([OH:14])[CH:13]=[CH2:1])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 75127Trimethylsulfonium iodideHCID 11008692(R)-tert-Butyldimethyl(oxiran-2-ylmethoxy)silaneHCID 178418339Butyllithium

Product 1

HCID 14185009(R)-1-(tert-butyldimethylsilanyloxy)-3-buten-2-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

n-Butyllithium (58.2 mL, 2.64 M solution in hexane) was added dropwise to a suspension of trimethylsulfonium iodide (32.4 g) in tetrahydrofuran (400 mL) in a nitrogen atmosphere at −20° C. The reaction solution was stirred at the same temperature for 30 minutes. tert-Butyldimethylsilyl (R)-(−)-glycidyl ether (10 g) was added dropwise to the reaction solution at the same temperature. The reaction solution was stirred for three hours with gradual heating to room temperature. Aqueous ammonium chloride and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride twice. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (9.6 g).

Workup

  1. stirringThe reaction solution was stirred for three hours
  2. customthe organic layer was separated
  3. washThe organic layer was washed with saturated aqueous sodium chloride twice
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a62754b568664137a70c172305fc4d61
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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