Sodium hydride → HCID 67502225, compound

HRID 921540Notes

Reaction equation

HRID 921540 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[NH:10][CH:11]=[C:12]([CH2:13][CH3:14])[C:5]=12.Cl[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=[C:12]([CH2:13][CH3:14])[C:5]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 67500967HCID 67500967, compound

Product 1

HCID 67502225HCID 67502225, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.877 g, a 55% dispersion in paraffin liquid) was added to a solution of compound (41c) (3.3 g) in DMF (61 mL) at 0° C., followed by stirring for 10 min. Then, [2-(chloromethoxy)ethyl]trimethylsilane (3.53 mL) was added to the reaction solution, followed by stirring at room temperature for 1 hr. After cooling, ice water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated saline in this order and was then dried over anhydrous sodium sulfate. After distillation of the solvent, the residue was purified by neutral silica gel column chromatography (n-hexane/ethyl acetate) to obtain compound (41d) (4.30 g, 76%) as a colorless oily substance.

Workup

  1. stirringby stirring at room temperature for 1 hr
  2. temperatureAfter cooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and saturated saline in this order
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. distillationAfter distillation of the solvent
  7. customthe residue was purified by neutral silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c115825ceae3472389ca938193849e58
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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