Dimethylformamide → HCID 21604654, compound

HRID 616301Notes

Reaction equation

HRID 616301 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:11]([CH3:13])[CH3:12])[CH2:9][OH:10])=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].[O:21]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:11]([CH3:13])[CH3:12])[CH2:9][O:10][CH2:31][C:30]2[CH:33]=[CH:34][CH:35]=[C:28]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:29]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 3478532-(4-chlorophenyl)-3-methylbutan-1-ol

Product 1

HCID 21604654HCID 21604654, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

2.0 g of 2-(4-chlorophenyl)-3-methylbutanol in 10 ml of a 20% mixture of dimethylformamide and toluene was added over a 5 minute period to sodium hydride (0.8 g, 50% in oil) in 20 ml of toluene at 110°-120° C, and the mixture was stirred for 15 minutes. 3.0 g of 3-phenoxybenzyl bromide in 15 ml of toluene was then added over a 15 minute period and the mixture was gently refluxed for 2 hours, then was cooled and 10 ml of mineral spirits was added. The mixture was poured into ice/hydrochloric acid, extracted with ether, washed with sodium bicarbonate solution and dried (MgSO4). The solvent was removed to give an orange oil, which was chromatographed on silica gel using 1:1 methylene dichloride:hexane as eluent to give 1.

Workup

  1. temperaturethe mixture was gently refluxed for 2 hours
  2. temperaturewas cooled
  3. extractionextracted with ether
  4. washwashed with sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed
  7. customto give an orange oil, which
  8. customwas chromatographed on silica gel using 1:1 methylene dichloride
  9. customhexane as eluent to give 1

Sources & evidence

ORD record
ord-32ca74a6d06741119c6954ef25bb066a
Source dataset
uspto-grants-1978_02
Patent number
US04073812

Reaction notes

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