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

HRID 1027958Notes

Reaction equation

HRID 1027958 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-d08e961d5f1a48ce9f1701549ff10665
Source dataset
uspto-grants-2014_05
Patent number
US08735401B2

Reaction notes

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