Sodium hydride → HCID 22003673, compound

HRID 324429Notes

Reaction equation

HRID 324429 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[NH:11][N:10]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Na+].[CH3:20][Si:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][O:24][CH2:25]Cl>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH2:25][O:24][CH2:23][CH2:22][Si:21]([CH3:28])([CH3:27])[CH3:20])[C:12]([C:14]([F:16])([F:17])[F:15])=[N:11][N:10]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 22003607HCID 22003607, compound

Product 1

HCID 22003673HCID 22003673, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of the product from step (ix) (17.46 g) in dry N,N-dimethylformamide (300 ml) was treated with 60% dispersion of sodium hydride (3.22 g) in portions at room temperature under nitrogen. After the initial effervescence had subsided the resultant orange oil was stirred for a further 30 min before being treated with 2-(trimethylsilyl)ethoxymethyl chloride (14.3 ml) dropwise giving a pale yellow suspension which was further stirred for 30 min. The mixture was carefully poured onto water (700 ml) and extracted with ethyl acetate (3×250 ml). The combined organic extracts were further washed with water (3×250 ml) and saturated brine (250 ml) before collecting, drying over magnesium sulphate and evapoaration of the solvent under reduced pressure to give the subtitle product as a yellow oil. Yield: 26.1 g. This was not purified but used directly in the next step.

Workup

  1. customdropwise giving a pale yellow suspension which
  2. stirringwas further stirred for 30 min
  3. additionThe mixture was carefully poured onto water (700 ml)
  4. extractionextracted with ethyl acetate (3×250 ml)
  5. washThe combined organic extracts were further washed with water (3×250 ml) and saturated brine (250 ml)
  6. custombefore collecting
  7. dry with materialdrying over magnesium sulphate and evapoaration of the solvent under reduced pressure

Sources & evidence

ORD record
ord-91b51ba1db864c69b43d17cb8182095b
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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