Potassium bis(trimethylsilyl)amide → HCID 59302569, compound

HRID 2237447Notes

Reaction equation

HRID 2237447 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([O:13][C:14]([N:16]1[CH2:22][CH2:21][C:20]2[CH:23]=[CH:24][S:25][C:19]=2[C:18](=O)[CH2:17]1)=[O:15])[CH3:12]>C1COCC1.CCOC(C)=O>[CH2:11]([O:13][C:14]([N:16]1[CH2:22][CH2:21][C:20]2[CH:23]=[CH:24][S:25][C:19]=2[C:18](=[CH2:1])[CH2:17]1)=[O:15])[CH3:12]

Participants

5

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 59302557HCID 59302557, compound

Product 1

HCID 59302569HCID 59302569, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

MePPh3 Br (785 mg, 2.2 mmol) was dissolved in 7 mL THF and treated with KHMDS (408 mg, 2.04 mmol). After stirring for 30 minutes, the product of step d) (350 mg, 1.5 mmol) was added as a solution in 3 mL THF. After stirring for 1 hour, the reaction was diluted with EtOAc and washed with water. The organic layer was concentrated and the product was purified by silica gel chromatography (EtOAc/Hex-gradient) to give 188 mg of the subtitle compound.

Workup

  1. stirringAfter stirring for 1 hour
  2. washwashed with water
  3. concentrationThe organic layer was concentrated
  4. customthe product was purified by silica gel chromatography (EtOAc/Hex-gradient)

Sources & evidence

ORD record
ord-8916104d8b37433687e483a12bec4ba5
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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