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

HRID 1288948Notes

Reaction equation

HRID 1288948 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-dioxolane

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 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 a 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-59215da115f54f09bde252b749189ff8
Source dataset
uspto-grants-1998_05
Patent number
US05747487

Reaction notes

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