Triethylamine → Tert-butyl(3-ethoxy-2,2-dimethylpropoxy)dimethylsilane

HRID 556521Notes

Reaction equation

HRID 556521 reaction equation
[Si:1]([O:8][CH2:9][C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:15](N(CC)CC)[CH3:16].CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>C1COCC1>[C:4]([Si:1]([O:8][CH2:9][C:10]([CH3:14])([CH3:13])[CH2:11][O:12][CH2:15][CH3:16])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 590121383-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropan-1-ol

Product 1

HCID 23090613Tert-butyl(3-ethoxy-2,2-dimethylpropoxy)dimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropan-1-ol (Registry No. 117932-70-4) (2.18 g, 10 mmol) in THF (30 ml) were added triethylamine (1.67 ml, 12 mmol) and methanesulfonyl chloride (0.85 ml, 11 mmol) under ice cooling. The reaction liquid was stirred at room temperature for 30 minutes, and to the reaction liquid was added an aqueous solution of sodium bicarbonate. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (2.98 g, quant.) as colorless oily substance.

Workup

  1. customThe reaction liquid
  2. customto the reaction liquid
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0c69297ad514922ba44667d65623687
Source dataset
uspto-grants-2011_11
Patent number
US08058280B2

Reaction notes

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