Chlorotrimethylsilane → HCID 68977387, compound

HRID 1948598Notes

Reaction equation

HRID 1948598 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][CH:5]=[C-:6][CH:7]=2)[O:2]1.[Mg+2].[Br-].C1(C)C=CC=CC=1.C1COCC1.[CH3:24][N:25]([CH3:38])[C:26]1(C#N)[CH2:35][CH2:34][C:29]2([O:33][CH2:32][CH2:31][O:30]2)[CH2:28][CH2:27]1.[Cl-].[NH4+].C[Si](C)(C)[Cl:43]>C1COCC1.CC(CC)=O.O>[ClH:43].[O:2]1[C:3]2[CH:4]=[CH:5][C:6]([C:26]3([N:25]([CH3:38])[CH3:24])[CH2:35][CH2:34][C:29]4([O:33][CH2:32][CH2:31][O:30]4)[CH2:28][CH2:27]3)=[CH:7][C:8]=2[O:9][CH2:1]1

Participants

9

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 25517Ammonium ChlorideHCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 44296443,4-(Methylenedioxy)phenylmagnesium bromide solutionHCID 22635083Tetrahydrofuran toluene

Product 1

HCID 68977387HCID 68977387, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1M 3,4-(methylenedioxy)phenylmagnesium bromide solution in toluene/THF (1:1) (62.5 ml, 62.5 mmole) was added dropwise at 5°-10° C. 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 (5.25 g, 25 mmole) in absolute THF (75 ml) and then stirred at RT for 20 hours. The reaction mixture was worked up by adding 20% ammonium chloride solution (20 ml) and water (25 ml) while cooling with ice and the mixture was extracted with ether (3×50 ml). The organic phase was washed with water and saturated sodium chloride solution, dried over sodium sulphate, and concentrated by evaporation in vacuo. A colourless oil (11.26 g) remained, which was dissolved in ethyl methyl ketone (35 ml) and to which trimethylchlorosilane (4.75 ml, 37.5 mmole) was added while cooling with ice. The mixture was stirred in an open flask for 5 hours at RT. A colourless solid then precipitated out, which was suction filtered and dried in air.

Workup

  1. temperaturewhile cooling with ice
  2. extractionthe mixture was extracted with ether (3×50 ml)
  3. washThe organic phase was washed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. additionwas added
  7. temperaturewhile cooling with ice
  8. stirringThe mixture was stirred in an open flask for 5 hours at RT
  9. customA colourless solid then precipitated out
  10. filtrationfiltered
  11. customdried in air

Sources & evidence

ORD record
ord-7b1799eee5b94ea48a0ab8a15c9579d6
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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