Chlorotrimethylsilane → HCID 57672309, compound

HRID 1645403Notes

Reaction equation

HRID 1645403 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH:12]([OH:14])[CH3:13].[CH3:15][Si:16]([CH3:19])([CH3:18])Cl.C[Si](C)(C)N[Si](C)(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH:12]([O:14][Si:16]([CH3:19])([CH3:18])[CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 57672310HCID 57672310, compound

Product 1

HCID 57672309HCID 57672309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The alcohol 49 (10 mmol) was dissolved in absolute THF (15 ml) with exclusion of moisture. Trimethylchlorosilane (2.1 ml, 15.3 mmol) and hexamethyldisilazane (4.9 ml, 23.3 mmol) were added, and the mixture was stirred at room temperature for 24 hours. The course of the reaction was monitored by thin layer chromatography. When the reaction had ended, the solvent was removed under vacuo. The remaining residue was a viscous oil which was taken up in diethyl ether (30 ml), and saturated NaHCO3 (30 ml) was added. The phases were separated, and the aqueous phase was extracted twice with 15 ml portions of Et2O. The combined organic phases were dried over Na2SO4 and concentrated under vacuo. The resulting product was initially in the form of an oil and crystallized spontaneously. The crude product was further purified by recrystallization from hexane.

Workup

  1. customthe solvent was removed under vacuo
  2. additionsaturated NaHCO3 (30 ml) was added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted twice with 15 ml portions of Et2O
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. concentrationconcentrated under vacuo
  7. customcrystallized spontaneously
  8. customThe crude product was further purified by recrystallization from hexane

Sources & evidence

ORD record
ord-650295bc888f4aac97cd3da509d87008
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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