Sodium hydride → HCID 68665588, compound

HRID 883077Notes

Reaction equation

HRID 883077 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[C:9]([O:13][C:14](=[O:44])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[C:19]([C:28]2[CH:37]=[C:36]3[C:31]([C:32]([CH3:42])([CH3:41])[CH2:33][C:34](=[O:40])[N:35]3[CH2:38][CH3:39])=[CH:30][C:29]=2[CH3:43])[CH:18]=1)([CH3:12])([CH3:11])[CH3:10]>CS(C)=O>[C:9]([O:13][C:14]([CH:15]1[CH2:2][CH:16]1[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:25])[F:26])=[C:19]([C:28]2[CH:37]=[C:36]3[C:31]([C:32]([CH3:42])([CH3:41])[CH2:33][C:34](=[O:40])[N:35]3[CH2:38][CH3:39])=[CH:30][C:29]=2[CH3:43])[CH:18]=1)=[O:44])([CH3:11])([CH3:10])[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 68666370HCID 68666370, compound

Product 1

HCID 68665588HCID 68665588, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a round bottom flask was added trimethylsulfoxonium iodide (2.8 mmol, 0.37 g) and 60% NaH (2.8 mmol, 0.07 g) and the flask was cooled to −10° C. with an ice-water bath. DMSO 92 ML) was then added dropwise. Initially some foamy suspension was observed. The cooling bath was removed and the reaction mixture was allowed to stir at r.t. for 30-40 min till the reaction mixture became a turbid solution. Compound 2B (0.17 mmol, 0.085 g) was then dissolved in 1.5 mL DMSO and was added to the reaction mixture. The golden yellow solution was stirred at 50° C. (oil bath) for 2 h. After cooling to r.t., the reaction mixture was poured into 50 mL of ice-water. It was extracted with EtOAc (3×15 mL). The organic layer was washed with water followed by brine and was then dried over Na2SO4. The solvent was filtered and evaporated in vacuo to obtain 2-[3-(1-ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-trifluoromethoxy-phenyl]-cyclopropanecarboxylic acid tert-butyl ester as a colorless oil. It was purified by preparative TLC with 3.5:1 hexanes-EtOAc as the eluting system to obtain 0.04 g of the product as a white foam. The product has the same Rf as the starting material. However, the product does not stain with KMnO4 stain indicating the disappearance of the double bond while the starting material does.

Workup

  1. customThe cooling bath was removed
  2. additionwas added to the reaction mixture
  3. stirringThe golden yellow solution was stirred at 50° C. (oil bath) for 2 h
  4. temperatureAfter cooling to r.t.
  5. extractionIt was extracted with EtOAc (3×15 mL)
  6. washThe organic layer was washed with water
  7. dry with materialwas then dried over Na2SO4
  8. filtrationThe solvent was filtered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d1be0e07e42d43328ffb238828aa7fff
Source dataset
uspto-grants-2012_08
Patent number
US08236819B2

Reaction notes

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