Chlorotrimethylsilane → HCID 86080031, compound

HRID 2252529Notes

Reaction equation

HRID 2252529 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:5][O:6][CH3:7])[CH2:3][OH:4].C(N(CC)CC)C.[CH3:16][Si:17](Cl)([CH3:19])[CH3:18]>ClCCl>[CH3:1][C:2]([CH3:8])([CH2:3][O:4][Si:17]([CH3:19])([CH3:18])[CH3:16])[CH2:5][O:6][CH3:7]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 1434401-Propanol, 3-methoxy-2,2-dimethyl-

Product 1

HCID 86080031HCID 86080031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g of 2,2-dimethyl-3-methoxy-1-propanol was dissolved in 20 ml of dichloromethane. The resultant solution was cooled in ice-water bath to below 5° C., and 1.65 ml of triethyl amine was added thereto. After stirring the mixture 5 minutes, 1.29 ml of trimethylsilyl chloride was added drop-wise to the reaction mixture, and the mixture was stirred in ice-water bath for further 2 hours, and at room temperature for further 1 hour. The reaction mixture was washed with water, and the organic layer separated was dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated to give 1.33 g of concentrate. The crude product was purified by column chromatography using petroleum ether as eluent, to give colorless pure compound.

Workup

  1. additionwas added drop-wise to the reaction mixture
  2. washThe reaction mixture was washed with water
  3. customthe organic layer separated
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate was evaporated
  7. customto give 1.33 g
  8. concentrationof concentrate
  9. customThe crude product was purified by column chromatography
  10. customto give colorless pure compound

Sources & evidence

ORD record
ord-5a4904a6119943f3aacb53eb82d7a59a
Source dataset
uspto-grants-2008_01
Patent number
US07323431B2

Reaction notes

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