Hydrochloric Acid → HCID 13397350, compound

HRID 1743274Notes

Reaction equation

HRID 1743274 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) δ 7.7 (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) δ 134.3, 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-6cfb91982bc347aaa50ece1c483635eb
Source dataset
uspto-grants-2006_03
Patent number
US07009015B2

Reaction notes

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