Propane → HCID 11182953, compound

HRID 1953174Notes

Reaction equation

HRID 1953174 reaction equation
C([Mg]Cl)(C)C.[C:6]([NH2:10])([CH3:9])([CH3:8])[CH3:7].CCC.[CH3:14][Si:15](OC)([O:18][CH3:19])[O:16][CH3:17]>O1CCCC1>[CH3:14][Si:15]([NH:10][C:6]([CH3:9])([CH3:8])[CH3:7])([O:18][CH3:19])[O:16][CH3:17]

Participants

6

Reactant 4

HCID 6334PropaneHCID 6385Tert-ButylamineHCID 14456MethyltrimethoxysilaneHCID 178418918HCID 178418918, compound2×

Product 1

HCID 11182953HCID 11182953, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A thermometer an addition funnel and a condenser were fitted to a stirrer-equipped one liter, four-necked flask. The flask was charged with one mol of isopropylmagnesium chloride in 500 ml of tetrahydrofuran (THF). The addition funnel was charged with 1.02 mol (75 g) of tert-butylamine which was slowly added to the stirred isopropylmagnesium chloride. The reaction was mildly exothermic and there was immediate evolution of propane gas. After completion of the addition (2 hours), the contents were refluxed for 30 minutes to complete the evolution of the gas. The reaction mixture was cooled to room temperature and one mol (135 g) of methyltrimethoxysilane was added to the stirred reaction mixture over a period of one hour. The reaction was mildly exothermic and the contents were refluxed at a pot temperature of 75° C. for 30 minutes to complete the reaction. The methyl(t-butylamino)dimethoxysilane was filtered under nitrogen atmosphere from the magnesium methoxychloride. The salt cake was washed with diethyl ether (2×200 ml) to obtain the residual methyl(t-butylamino)dimethoxysilane. The solvent was distilled to a pot temperature of 90° C. and the residue was distilled under reduced pressure to yield 138 g of methyl(t-butylamino)dimethoxysilane as a colorless oil (purity>98%); bp 107° C./135 mm. The yield was 82% of theoretical.

Workup

  1. customA thermometer an addition funnel and a condenser were fitted to a stirrer-equipped one liter, four-necked flask
  2. additionAfter completion of the addition (2 hours)
  3. temperaturethe contents were refluxed for 30 minutes
  4. temperaturethe contents were refluxed at a pot temperature of 75° C. for 30 minutes
  5. customthe reaction
  6. filtrationThe methyl(t-butylamino)dimethoxysilane was filtered under nitrogen atmosphere from the magnesium methoxychloride
  7. washThe salt cake was washed with diethyl ether (2×200 ml)

Sources & evidence

ORD record
ord-ae3083c471df4868a593e5c98105c3c5
Source dataset
uspto-grants-2000_09
Patent number
US06114558

Reaction notes

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