Dimethylformamide → 3-(4,4'-Dimethoxytrityloxy)methyl-5-fluoromethylbenzylazide

HRID 473240Notes

Reaction equation

HRID 473240 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([CH2:13][F:14])[CH:12]=1)[CH2:8][OH:9])=[N+:2]=[N-:3].[C:15](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:24]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[CH:26][CH:25]=1)[C:16]1[CH:23]=[CH:22][C:19]([O:20][CH3:21])=[CH:18][CH:17]=1.CN(C=O)C>N1C=CC=CC=1>[CH3:29][O:28][C:27]1[CH:26]=[CH:25][C:24]([C:15]([O:9][CH2:8][C:7]2[CH:6]=[C:5]([CH:12]=[C:11]([CH2:13][F:14])[CH:10]=2)[CH2:4][N:1]=[N+:2]=[N-:3])([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:16]2[CH:23]=[CH:22][C:19]([O:20][CH3:21])=[CH:18][CH:17]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 866715183-Azidomethyl-5-fluoromethylbenzylalcohol

Product 1

HCID 866715193-(4,4'-Dimethoxytrityloxy)methyl-5-fluoromethylbenzylazide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

From a reaction system containing 3-Azidomethyl-5-fluoromethylbenzylalcohol (36) (142 mg, 0.73 mmol), the air was evacuated and then Ar was charged therein. To this were added DMTrCl (323 mg, 0.95 mmol), DMF (2.0 mL), and pyridine (2.0 mL), and stirred for 22 hours at a room temperature. TLC was used to confirm the progress of the reaction. Then, the solvent was removed in vacuo. The residue was subjected to extraction with EtOAc. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to remove the solvent. The residue was purified by neutral silica gel column chromatography (hexane:EtOAc=20:1 to 5:1) to isolate

Workup

  1. customthe air was evacuated
  2. additionAr was charged
  3. customthe progress of the reaction
  4. customThen, the solvent was removed in vacuo
  5. extractionThe residue was subjected to extraction with EtOAc
  6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by neutral silica gel column chromatography (hexane:EtOAc=20:1 to 5:1)
  11. customto isolate

Sources & evidence

ORD record
ord-47430a3c2d1a4af5b8a28ed05ff37a15
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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