Dimethyl Sulfoxide → HCID 59455175, compound

HRID 1045552Notes

Reaction equation

HRID 1045552 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

The title compound was prepared by following general procedure 3. DMSO was added to NaH (1 equiv.) and heated to 65° C. for 1 h. THF was added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture was cooled to 0° C. Trimethylsulfonium iodide (1 equiv.) was added and stirred for 10 min. after which the solution of cyclopropyl(4-fluorophenyl) methanone (1 equiv.) in THF was added dropwise. After complete addition, the reaction mixture was stirred at RT for 2 h. The product was detected by LCMS and the reaction mixture was poured into ice water, extracted in diethyl ether (4×50 mL), dried over Na2SO4 and concentrated at 25° C. to obtain the product.

Workup

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture was cooled to 0° C
  3. additionwas added dropwise
  4. additionAfter complete addition
  5. extractionextracted in diethyl ether (4×50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated at 25° C.
  8. customto obtain the product

Sources & evidence

ORD record
ord-dd0aa9595d1f46a1add804db97198ec0
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Reaction notes

Loading…