Chlorotrimethylsilane → HCID 86080031, compound

HRID 748558Notes

Reaction equation

HRID 748558 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 for 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 concentrated 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. waitat room temperature for further 1 hour
  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. concentrationthe filtrate was concentrated
  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-29c0091f1b7547f58b337dd94f08672d
Source dataset
uspto-grants-2008_07
Patent number
US07399812B2

Reaction notes

Loading…