Hexane → 2-[2-[(2-Nitrophenyl)methyl]3-thienyl]-1,3-dioxolane

HRID 1457632Notes

Reaction equation

HRID 1457632 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][C:10]=1[CH:11]1[O:15][CH2:14][CH2:13][O:12]1)CCC.[N+:24]([C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29]Br)([O-:26])=[O:25].CCCCCC>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:24]([C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[CH:11]1[O:12][CH2:13][CH2:14][O:15]1)([O-:26])=[O:25]

Participants

6

Reactant 3

HCID 8058HexaneHCID 77569alpha-Bromo-2-nitrotolueneHCID 111340582-(Tributylstannyl)-3-thienyl-1,3-dioxolane

Product 1

HCID 111300652-[2-[(2-Nitrophenyl)methyl]3-thienyl]-1,3-dioxolaneYield 77.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-[2-(tributylstannyl)-3-thienyl]-1,3-dioxolane (8.8 gms, 20 mmols), 2-nitrobenzyl bromide (4.5 gms, 22 mmol) and tetrakis (triphenylphosphine)-palladium (0) (200 mg) is refluxed in degassed toluene for 16 hours under a nitrogen atmosphere. At the end, the reaction mixture is cooled to room temperature and filtered through diatomaceous earth. The toluene is removed by concentrating at reduced pressure and the product isolated by silica gel column chromatography by elution with 30% ethyl acetate: hexane to give 4.5 gms of the desired product as viscous liquid. Mass Spectrum; M+ 292

Workup

  1. filtrationfiltered through diatomaceous earth
  2. customThe toluene is removed
  3. concentrationby concentrating at reduced pressure
  4. customthe product isolated by silica gel column chromatography by elution with 30% ethyl acetate

Sources & evidence

ORD record
ord-eac0e902185e4055b653d916e3c5512d
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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