Chlorotrimethylsilane → HCID 21848599, compound

HRID 618886Notes

Reaction equation

HRID 618886 reaction equation
[F:1][C:2]([F:29])([C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])[CH:3]([C:5]1[NH:6][C:7]([CH:10]([OH:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])=[CH:8][CH:9]=1)[OH:4].[H-].[Na+].[H][H].[CH3:34][Si:35](Cl)([CH3:37])[CH3:36]>C1COCC1>[F:29][C:2]([F:1])([C:22]([F:27])([F:28])[C:23]([F:26])([F:24])[F:25])[CH:3]([C:5]1[NH:6][C:7]([CH:10]([O:21][Si:35]([CH3:37])([CH3:36])[CH3:34])[C:11]([F:19])([F:20])[C:12]([F:17])([F:18])[C:13]([F:15])([F:14])[F:16])=[CH:8][CH:9]=1)[O:4][Si:35]([CH3:37])([CH3:36])[CH3:34]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydrideHCID 18694739HCID 18694739, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21848599HCID 21848599, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Recrystallized 2,5-bis(2',2',3',3',4',4',4'-heptafluoro-1'-hydroxybutyl)pyrrole (0.5 mmol, 0.2316 g) was dissolved in 25 ml of dry THF and transferred to a cooled (0° C.) suspension of sodium hydride (1.0 mmol, 0.024 g) in 60 mL of THF. When hydrogen evolution ceased (after 1 hour) trimethylsilyl chloride (1 mmol, 0.109 g) was added by syringe. The mixture became cloudy and was stirred at room temperature for 1 hour before the solvent was removed in vacuo. The remaining residue was partitioned between 10% sodium bicarbonate solution and pentane. The organic layer was washed twice with water and dried over magnesium sulfate, filtered and evaporated to leave a colorless oil (0.204 g, 0.34 mmol, 67%). 1H NMR (CDCl3, 360 MHz) 8.68 (broad s, 1 H); 6.15 (d, 2 H, J=2.7 Hz); 5.13 (dd, 2 H, J1-18.8 Hz, J2=5.0 Hz); 0.03 (s, 18 H).

Workup

  1. temperaturea cooled
  2. additionwas added by syringe
  3. customwas removed in vacuo
  4. customThe remaining residue was partitioned between 10% sodium bicarbonate solution and pentane
  5. washThe organic layer was washed twice with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a60728b7715c4b1ab7b40b6e73dfb6f0
Source dataset
uspto-grants-1999_09
Patent number
US05955603

Reaction notes

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