Sodium hydride → 3-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropan-1-ol

HRID 1010527Notes

Reaction equation

HRID 1010527 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[H-].[Na+].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C(=O)(O)[O-].[Na+]>O1CCCC1>[Si:10]([O:4][CH2:3][C:2]([CH3:7])([CH3:1])[CH2:5][OH:6])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 31344Neopentyl glycolHCID 516892Sodium Bicarbonate

Product 1

HCID 590121383-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropan-1-olYield 87.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10 g of 2,2-dimethyl-1,3-propanediol in 100 ml of tetrahydrofuran is added in drops to a suspension of 3.85 g of sodium hydride (60%) in 30 ml of tetrahydrofuran. It is allowed to stir for 45 more minutes, and then 14.5 g of tert-butyldimethylsilyl chloride is added. Then, it is stirred for one more hour at 25° C. Then, the reaction mixture is poured into saturated sodium bicarbonate solution. It is extracted with ethyl acetate, the organic phase is washed with saturated sodium chloride solution, dried on sodium sulfate, and concentrated by evaporation in a vacuum. The crude product is purified by column chromatography on silica gel. 18.4 g of product is obtained.

Workup

  1. stirringThen, it is stirred for one more hour at 25° C
  2. extractionIt is extracted with ethyl acetate
  3. washthe organic phase is washed with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6af964484a92476bb66e3b0f47a4d98a
Source dataset
uspto-grants-2011_07
Patent number
US07977325B2

Reaction notes

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