Dimethyl Sulfoxide → HCID 59455175, compound

HRID 1401437Notes

Reaction equation

HRID 1401437 reaction equation
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[CH:12]1([C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:16])[CH2:14][CH2:13]1>C1COCC1>[CH:12]1([C:15]2([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[CH2:8][O:16]2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 69876Cyclopropyl 4-fluorophenyl ketoneHCID 75127Trimethylsulfonium iodide

Product 1

HCID 59455175HCID 59455175, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

DMSO is added to NaH (1-1.8 equiv.) and heated to 65° C. for 1 h. THF is added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture is cooled to 0° C. Trimethylsulfonium iodide (1-1.2 equiv.) is added and the contents are stirred for 10 min. after which the solution of cyclopropyl(4-fluorophenyl)methanone (1 equiv.) in THF is added dropwise. After complete addition, the reaction mixture is stirred at RT for 2 h; the reaction is monitored by LCMS. After completion, the reaction mixture is poured in ice water, extracted in diethyl ether, dried over sodium sulfate and concentrated at 25° C. to get the crude product.

Workup

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture is cooled to 0° C
  3. additionis added dropwise
  4. additionAfter complete addition
  5. extractionextracted in diethyl ether
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated at 25° C.

Sources & evidence

ORD record
ord-71a96a052e164e81bb8afab5d17a1929
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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