Hydrochloric Acid → HCID 13397350, compound

HRID 2086385Notes

Reaction equation

HRID 2086385 reaction equation
[CH2:1]([Si:4](OC)([O:7][CH3:8])[O:5][CH3:6])[CH2:2][CH3:3].[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[SiH4].Cl>CCOCC>[C:11]1([Si:4]([CH2:1][CH2:2][CH3:3])([O:7][CH3:8])[O:5][CH3:6])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 23953SilaneHCID 61254TrimethoxypropylsilaneHCID 178418255HCID 178418255, compound

Product 1

HCID 13397350HCID 13397350, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A 500 mL round bottomed flask was charged with propyl-trimethoxysilane (19.3 mL, 1.10×10−1 mole, Hüls) and ether (250 mL, Aldrich). A pressure equalizing addition funnel was charged with phenylmagnesium bromide (33.3 mL of a 3M solution in ether, 99.9 mmol, Aldrich) and ether (50 mL). The contents of the addition funnel were added into the silane over a 20 minute period (exotherm). A white precipitate formed. The reaction was stirred for two hours at room temperature then poured into 0.2N HCl (300 mL). The layers were separated, the product extracted into ether (2×250 mL), dried (MgSO4), and filtered. The solvent was removed via rotary evaporation resulting in 23.5 grams of crude material. Distillation under reduced pressure (b.p. 71° C., 0.6 mm Hg) provided phenyl-propyl-dimethoxysilane (18.5 g, 88.0 mmol, 88% yield); C11H18SiO2 (mw=210.34); 1H NMR (CDCl3) δ7.7 (m, 2H), 7.4 (m, 3H), 3.6 (s, 6H), 1.4 (m, 2H), 1.0 (t, 3H), 0.9 (t, 2H); 13C NMR (CDCl3) δ134.3, 133.3, 130.1, 127.9, 50.6, 17.9, 16.3, 14.8; MS m/z (relative abundance) 210 (2), 167 (100), 137 (33), 107 (17), 91 (17), 59 (10).

Workup

  1. additionaddition funnel
  2. customA white precipitate formed
  3. customThe layers were separated
  4. extractionthe product extracted into ether (2×250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe solvent was removed via rotary evaporation
  8. customresulting in 23.5 grams of crude material
  9. distillationDistillation under reduced pressure (b.p. 71° C., 0.6 mm Hg)

Sources & evidence

ORD record
ord-60c682c63da54eb79755fb6b6647b4d9
Source dataset
uspto-grants-2004_04
Patent number
US06723865B2

Reaction notes

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