Water → HCID 18327740, compound

HRID 1250258Notes

Reaction equation

HRID 1250258 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][CH:13]([OH:17])[CH2:14][CH:15]=[CH2:16].O>C(N(CC)CC)C.C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:16]=[CH:15]/[CH2:14][CH:13]([OH:17])[CH3:12])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

8

Reactant 3

HCID 962WaterHCID 122474-Penten-2-OLHCID 1235464-Bromo-2-nitrotoluene

Product 1

HCID 18327740HCID 18327740, compoundYield 77.4%

Reagents, catalysts & solvents 4

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-bromo-2-nitrotoluene (2.16 g, 10.0 mmol), 4-penten-2-ol (904 mg, 10.5 mmol), palladium(II) acetate (22 mg, 0. 10 mmol) and tri-o-tolylphosphine (122 mg, 0.400 mmol) was diluted with triethylamine (3 mL) and acetonitrile (6 mL) and refluxed under nitrogen for 28 h. The mixture was poured into water (30 mL) and extracted with chloroform (2×30 mL). The chloroform extracts were dried (Na2SO4) and evaporated, and the residue was column chromatographed on 100 g of Merck silica gel 60 (70-230 mesh) with 20-40% (v/v) ethyl acetate, 20% (v/v) chloroform in hexane. This gave 1.71 g (77.4% yield) of yellow oil.

Workup

  1. temperaturerefluxed under nitrogen for 28 h
  2. extractionextracted with chloroform (2×30 mL)
  3. dry with materialThe chloroform extracts were dried (Na2SO4)
  4. customevaporated
  5. customchromatographed on 100 g of Merck silica gel 60 (70-230 mesh) with 20-40% (v/v) ethyl acetate, 20% (v/v) chloroform in hexane

Sources & evidence

ORD record
ord-d645431bdd854d0f9288b697219052ff
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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