Chlorotrimethylsilane → HCID 19974944, compound

HRID 1451518Notes

Reaction equation

HRID 1451518 reaction equation
[CH3:1][Li].C[Si](Cl)(C)C.[Br:8][C:9]1[CH:34]=[CH:33][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=3)[C:16]([CH:25]=[CH:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:15]2[CH3:32])=[CH:11][CH:10]=1.[NH4+].[Cl-]>CCOCC.C1COCC1>[Br:8][C:9]1[CH:34]=[CH:33][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=3)[C:16]([CH:25]([CH3:1])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:15]2[CH3:32])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 25517Ammonium ChlorideHCID 54298386HCID 54298386, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 19974944HCID 19974944, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a 0° C. suspension of cuprous iodide (12.7 g, 67.0 mmol) in 150 mL ether was added CH3Li (1.4M in ether, 96 mL, 134 mmol). The solution was cooled to -78° C. and treated with TMSCl (8.5 mL, 67 mmol) and a solution of the unsaturated ester from Step 3 (6.79 g, 15.8 mmol) in 30 mL of THF. The yellow suspension was allowed to warm to room temperature and was stirred 2.5 h. The reaction mixture was poured into saturated NH4Cl and extracted with EtOAc. The organic extracts were washed with water and brine and dried over Na2SO4. Purification by flash chromatography (20% ethyl acetate/hexanes) provided 5.13 g of the title product as a crystaline solid.

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customPurification by flash chromatography (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cbe3cc555118478e8ebbb18f459c0fba
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

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