Trimethoxypropylsilane → HCID 22238659, compound

HRID 2086388Notes

Reaction equation

HRID 2086388 reaction equation
[Mg].Br[C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:10].[CH2:11]([Si:14](OC)([O:17][CH3:18])[O:15][CH3:16])[CH2:12][CH3:13]>CCOCC>[CH3:10][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH3:9])[C:3]=1[Si:14]([CH2:11][CH2:12][CH3:13])([O:17][CH3:18])[O:15][CH3:16]

Participants

5

Reactant 3

HCID 61254TrimethoxypropylsilaneHCID 684712-Bromo-m-xyleneHCID 5462224Magnesium

Product 1

HCID 22238659HCID 22238659, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 500 mL round bottomed flask was charged with magnesium powder (2.1 g, 86 mmol, Aldrich) and ether (250 mL, Aldrich). 2-Bromo-m-xylene (9.0 mL, 68 mmol, Aldrich) was added over a 25 minute period. The contents were refluxed overnight (18 hours). The brown solution was cooled to room temperature and propyl-trimethoxysilane (17.8 mL, 101 mmol) was added over 20 minutes. A white precipitate formed. The contents were stirred at room temperature overnight (18 hours). The reaction was poured into 0.2N aqueous HCI (500 mL), the layers were separated and the product extracted into ether (3×150 mL). The combined organic portions were dried (MgSO4), filtered, and the solvent removed via rotary evaporation (13.5 g crude). Distillation under reduced pressure (b.p. 57° C., 0.04 mm Hg) provided (2,6-dimethylphenyl)-propyl-dimethoxysilane (6.8 g, 28 mmol, 41% yield); C13H22SiO2 (Mw=238.40); 1H NMR (CDCl3) δ7.2 (t, 1H), 7.0 (d, 2H), 3.6 (s, 6H), 2.5 (s, 6H), 1.4 (m, 2H), 1.0 (t, 3H), 0.9 (t, 2H); 13C NMR (CDCl3) δ145.2, 131.0, 129.6, 128.0, 49.8, 23.4, 17.9, 16.7, 16.3; MS m/z (relative abundance) 238 (8), 195 (100), 165 (22), 133 (12), 119 (10), 105 (13), 91 (9), 59 (16).

Workup

  1. temperatureThe contents were refluxed overnight (18 hours)
  2. customA white precipitate formed
  3. additionThe reaction was poured into 0.2N aqueous HCI (500 mL)
  4. customthe layers were separated
  5. extractionthe product extracted into ether (3×150 mL)
  6. dry with materialThe combined organic portions were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed via rotary evaporation (13.5 g crude)
  9. distillationDistillation under reduced pressure (b.p. 57° C., 0.04 mm Hg)

Sources & evidence

ORD record
ord-1eac1db3a2e14c9cb6f8d142cb443955
Source dataset
uspto-grants-2004_04
Patent number
US06723865B2

Reaction notes

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