Sodium hydride → 5-Chloro-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran

HRID 400657Notes

Reaction equation

HRID 400657 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[Cl:9][C:10]1[CH:11]=[C:12]([C:19]([CH3:28])([CH3:27])[CH2:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[C:13]2[O:17][CH2:16][CH2:15][C:14]=2[CH:18]=1>CS(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([C:19]([CH3:28])([CH3:27])[CH2:20][C:21]2([C:22]([F:23])([F:24])[F:25])[CH2:2][O:26]2)[C:13]2[O:17][CH2:16][CH2:15][C:14]=2[CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 469392144-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one

Product 1

HCID 600263575-Chloro-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuranYield 91.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of trimethylsulfoxonium iodide (343 mg, 1.56 mmol) in 3 mL of anhydrous DMSO was treated with NaH (60% in mineral oil, 66.0 mg, 1.65 mmol) in portions and the mixture was stirred at room temperature for 30 minutes. The mixture was transferred to a solution of 4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one (400 mg, 1.30 mmol) in 1 mL of anhydrous DMSO over 5 minutes and the resulting mixture was stirred overnight. The mixture was quenched with water and extracted with three 20 mL portions of ethyl acetate. The combined organic layers were washed with two 5 mL portions of water, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 380 mg (91% yield) of the title product as a yellow oil. The crude product was sufficiently pure and used without further purification.

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. customThe mixture was quenched with water
  3. extractionextracted with three 20 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with two 5 mL portions of water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d38df95cc6546d59c8767e119742b63
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

Loading…