Dimethylformamide → HCID 13367633, compound

HRID 1583589Notes

Reaction equation

HRID 1583589 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])=[CH:6][CH:5]=1.CN(C)C=O.[F:20][CH2:21][CH2:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.O>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:14])([CH3:13])[CH2:11][O:12][CH2:28][C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:22][CH2:21][F:20])=[CH:31][CH:30]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 132166942,2-Dimethyl-2-(4-methylphenyl)ethanolHCID 202592671-(Chloromethyl)-4-(2-fluoroethoxy)benzene

Product 1

HCID 13367633HCID 13367633, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Procedure

Sodium hydride (0.9 g; 60% in oil) was added to 20 ml of toluene, and with heating, a solution of 2.5 g of 2-(4-methylphenyl)-2-methylpropyl alcohol in 10 ml of a mixture of 25% dimethylformamide and toluene was added dropwise over the course of 15 minutes. The mixture was stirred for 10 minutes, and then a solution of 2.9 g of 4-(2-fluoroethoxy)benzyl chloride in 10 ml of toluene was added dropwise over the course of 20 minutes. The mixture was further heated under reflux for 1 hour. The reaction mixture was cooled to room temperature, poured into water, and then extracted with toluene. The toluene layer was washed with water and dried over anhydrous sodium sulfate. Toluene was evaporated under reduced pressure. The resulting crude ether was purified by silica gel (100 g) column chromatography (developing solvent: a 2:1 mixture of toluene and n-hexane) to give 3.3 g of the desired 4-(2-fluoroethoxy)benzyl 2-(4-methylphenyl)-2-methylpropyl ether.

Workup

  1. temperaturewith heating
  2. temperatureThe mixture was further heated
  3. temperatureunder reflux for 1 hour
  4. extractionextracted with toluene
  5. washThe toluene layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customToluene was evaporated under reduced pressure
  8. customThe resulting crude ether was purified by silica gel (100 g) column chromatography (
  9. additiona 2:1 mixture of toluene and n-hexane)

Sources & evidence

ORD record
ord-0b24da9ec004461caedff9a51647f70e
Source dataset
uspto-grants-1985_11
Patent number
US04552894

Reaction notes

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