Chlorotrimethylsilane → HCID 21848610, compound

HRID 618887Notes

Reaction equation

HRID 618887 reaction equation
[F:1][C:2]([F:17])([C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)[OH:4].[H-].[Na+].[CH3:20][Si:21](Cl)([CH3:23])[CH3:22]>C1COCC1>[F:17][C:2]([F:1])([C:10]([F:15])([F:16])[C:11]([F:12])([F:13])[F:14])[CH:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)[O:4][Si:21]([CH3:23])([CH3:22])[CH3:20]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydrideHCID 104006151H-Pyrrol-2-yl(perfluoropropyl)methanol

Product 1

HCID 21848610HCID 21848610, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2',2',3',3',4',4',4'-heptafluoro-1'-hydroxybutyl)pyrrole (2.6514 g, 10 mmol) dissolved in 25 ml of dry THF was transferred by canula to a suspension of sodium hydride (0.2640 g, 11 mmol) in 50 ml of THF. The mixture was stirred for 2 hours at room temperature. Trimethylsilyl chloride (1.195 g, 11 mmol) was added dropwise and the solution was stirred overnight. The resulting suspension was evaporated almost to dryness and 50 ml of water was added. The mixture was extracted 3×50 mL with pentane and the organic layers were combined and dried over magnesium sulfate. Upon standing the MgSO4 withdraw a brown impurity from solution leaving a colorless organic layer. The solvent was evaporated leaving a light brown oil (3.128 g). 1H NMR showed that the crude material was 96% product by weight. The overall yield was therefore calculated to be 89%. 1H NMR (CDCl3, 360 MHz) 8.43 (broad s, 1 H); 6.83 (m, 1 H); 6.22 (m, 1 H) 6.17 (q, 1 H, J=2.8 Hz) 5.16 (dd, 1 H, J1=18.5 Hz, J2=5.8 Hz); 0.03 (s, 9 H).

Workup

  1. stirringthe solution was stirred overnight
  2. customThe resulting suspension was evaporated almost to dryness and 50 ml of water
  3. additionwas added
  4. extractionThe mixture was extracted 3×50 mL with pentane
  5. dry with materialdried over magnesium sulfate
  6. customwithdraw a brown impurity from solution
  7. customleaving a colorless organic layer
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9aa731ca60f545adbe7005ca66724d2a
Source dataset
uspto-grants-1999_09
Patent number
US05955603

Reaction notes

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