Water → 3-(4,4'-Dimethoxytrityloxymethyl)benzonitrile

HRID 473224Notes

Reaction equation

HRID 473224 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[CH3:11][O:12][C:13]1[CH:34]=[CH:33][C:16]([C:17](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1.O>CN(C=O)C.N1C=CC=CC=1>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]([O:1][CH2:2][C:3]2[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=2)[C:6]#[N:7])([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:16]2[CH:33]=[CH:34][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 962WaterHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 27346773-(Hydroxymethyl)benzonitrile

Product 1

HCID 683131823-(4,4'-Dimethoxytrityloxymethyl)benzonitrileYield 91%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (23 mL) and pyridine (23 mL), suspended were 3-hydroxymethylbenzonitrile (1.12 g, 8.38 mmol) and 4,4′-dimethoxytritylchloride (3.41 g, 10.06 mmol). The suspension was stirred for 12 hours at a room temperature under Ar atmosphere. TLC was used to confirm there was no starting material in the reaction mixture. Then, to the suspension was added iced water (20 mL). The mixture was subjected to extraction with EtOAc and water. The organic layer was washed with sat. NaCl aq., dried over anhydrous Na2SO4, and evaporated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (Hex:EtOAc=10:1) to give 3-(4,4′-dimethoxytrityloxymethyl)benzonitrile (4) (3.31 mg, 91%) as a colorless oil.

Workup

  1. extractionThe mixture was subjected to extraction with EtOAc and water
  2. washThe organic layer was washed with sat. NaCl aq.
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=10:1)

Sources & evidence

ORD record
ord-94d49bc746c9481790600c1a8ec346d3
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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