Dimethylformamide → HCID 68460417, compound

HRID 499730Notes

Reaction equation

HRID 499730 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14]C)=CC=2)[S:4][C:3]=1[CH2:16][CH2:17][OH:18].[CH3:19]N(C=O)C.[C:24](Cl)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:44](N(CC)CC)[CH3:45]>CN(C)C1C=CN=CC=1.O.C(Cl)Cl>[Br:1][C:2]1[C:6]([CH3:19])=[C:5]([C:7]2[CH:8]=[CH:13][C:12]([CH2:11][CH3:14])=[CH:45][CH:44]=2)[S:4][C:3]=1[CH2:16][CH2:17][O:18][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 68460883HCID 68460883, compound

Product 1

HCID 68460417HCID 68460417, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Under a nitrogen stream, to a solution of 2-[3-bromo-5-((4-ethylphenyl)methyl)thiophen-2-yl]-ethanol (2.55 g, 7.84 mmol) in a mixture of anhydrous DMF (15 ml) and methylene chloride (15 ml), trityl chloride (3.29 g, 11.8 mmol) was added. To this solution, triethylamine (1.64 ml, 11.8 mmol) and 4-dimethylaminopyridine (77 mg, 0.63 mmol) were added at 0° C. The reaction mixture was stirred at 40° C. for 4 hours. After addition of water, the reaction mixture was extracted with methylene chloride. The organic layer was washed with saturated aqueous sodium chloride and dried over sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:20)) to give the titled compound (3.60 g, 81%).

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:20))

Sources & evidence

ORD record
ord-cca0b401bb484f2fb6fe8ea24dc6f201
Source dataset
uspto-grants-2010_08
Patent number
US07767651B2

Reaction notes

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