Sodium hydride → HCID 14352181, compound

HRID 2275216Notes

Reaction equation

HRID 2275216 reaction equation
[H-].[Na+].[OH:3][CH2:4][C@H:5]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]1[CH2:12][OH:13].[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(=O)([O-])O.[Na+]>C1COCC1>[Si:18]([O:13][CH2:12][CH:6]1[O:7][C:8]([CH3:10])([CH3:11])[O:9][CH:5]1[CH2:4][OH:3])([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 78524473346-74-4

Product 1

HCID 14352181HCID 14352181, compoundYield 95,801.797%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To THF (50 mL), NaH (1.41 g, 0.032 mmol) was added at room temperature, followed by addition of ((4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (5.0 g, 0.031 mmol) at room temperature. The mixture was stirred at room temperature for 1 hr. After that, TBSCl (5.11 g, 0.034 mmol) was added at room temperature and stirred at room temperature overnight. The reaction solution was added with saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (8.21 g, 96%).

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customThe residues obtained
  5. concentrationafter concentration under reduced pressure
  6. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-96e730530b2c452caa63cca8283d8a66
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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