Sodium hydride → 2-(((Tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol

HRID 83571

Reaction equation

HRID 83571 reaction equation
[H-].[Na+].[CH2:3]=[C:4]([CH2:7][OH:8])[CH2:5][OH:6].[C:9]([Si:13]([CH3:16])([CH3:15])Cl)([CH3:12])([CH3:11])[CH3:10].[Cl-].[NH4+]>O1CCCC1>[Si:13]([O:6][CH2:5][C:4](=[CH2:3])[CH2:7][OH:8])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 770481,3-Propanediol, 2-methylene-

Product 1

HCID 112064702-(((Tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon atmosphere, to a suspension of sodium hydride (490 mg, 60 wt. % oil dispersion) in tetrahydrofuran (10 ml) were sequentially added 2-methylene-1,3-propanediol (1 ml) and tert-butyldimethylchlorosilane (2.22 g) at 0° C., and then the mixture was stirred at room temperature for 1 hour. To this reaction mixture was added a saturated aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. This organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1) to give the titled compound (1.62 g).

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThis organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-744fd6db4a024650b5257babfba9884b
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Linked notes

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