Sodium hydride → HCID 10727826, compound

HRID 1975323Notes

Reaction equation

HRID 1975323 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[H][H].[F:11][C:12]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:13]=1[CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20]>CS(C)=O>[F:11][C:12]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:13]=1[CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][C:16]21[O:20][CH2:2]2

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10656042HCID 10656042, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10727826HCID 10727826, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Trimethylsulfoxonium iodide (4.86 g, 22.1 mmol, 1.3 eq) was dissolved in DMSO (25 ml) and sodium hydride (0.49 g, 20.4 mmol, 1.2 eq) was added at 100° C. while being stirred. The solution was warmed to room temperature and stirred for 45 min while being stirred; thereafter, the solution became transparent. After terminal evolution of hydrogen had been confirmed, the solution was again heated at 10° C. and 2-(2,4-difluorobenzyl)cyclopentanone (3.56 g, 17.0 mmol, 1.0 eq) was dripped into the solution.

Workup

  1. stirringstirred for 45 min
  2. stirringwhile being stirred
  3. temperaturethe solution was again heated at 10° C.

Sources & evidence

ORD record
ord-d0327d79914848f4b068d23afe4afc86
Source dataset
uspto-grants-1994_02
Patent number
US05286737

Reaction notes

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