Chlorotrimethylsilane → HCID 68842549, compound

HRID 1948608Notes

Reaction equation

HRID 1948608 reaction equation
[C:1]1([CH2:7]C[Mg][Cl:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][N:12]([CH3:25])[C:13]1([C:23]#N)[CH2:22][CH2:21][C:16]2([O:20][CH2:19][CH2:18][O:17]2)[CH2:15][CH2:14]1.[Cl-].[NH4+].Cl[Si](C)(C)C>C1COCC1.O>[ClH:10].[CH3:11][N:12]([CH3:25])[C:13]1([CH2:23][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:22][CH2:21][C:16]2([O:20][CH2:19][CH2:18][O:17]2)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 25517Ammonium ChlorideHCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 178418865HCID 178418865, compound

Product 1

HCID 68842549HCID 68842549, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1M 2-phenylethylmagnesium chloride solution in THF (550 ml, 550 mmole) was added within 15 minutes under argon and while cooling with ice to a solution of 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (39 g, 186 mmole) in THF (300 ml) and the mixture was then stirred for 16 hours at room temperature. The reaction mixture was worked up by adding saturated ammonium chloride solution (295 ml) and water (120 ml) while cooling with ice, and was extracted with diethyl ether (3×150 ml). The organic phase was washed with water (100 ml) and saturated NaCl solution (100 ml) and then concentrated by evaporation. A brown oil remained (60.4 g). The crude product was dissolved in ethyl methyl ketone (310 ml) and ClSiMe3 (35.6 ml, 282 mmole) was added while cooling with ice. After 16 hours at RT the resultant solid product was suction filtered and washed with ethyl methyl ketone.

Workup

  1. temperaturewhile cooling with ice
  2. extractionwas extracted with diethyl ether (3×150 ml)
  3. washThe organic phase was washed with water (100 ml) and saturated NaCl solution (100 ml)
  4. concentrationconcentrated by evaporation
  5. dissolutionThe crude product was dissolved in ethyl methyl ketone (310 ml)
  6. temperaturewhile cooling with ice
  7. waitAfter 16 hours at RT the resultant solid product was
  8. filtrationsuction filtered
  9. washwashed with ethyl methyl ketone

Sources & evidence

ORD record
ord-571ceb061d4f4a45a78121b4f4a5ad22
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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