Water → HCID 18327739, compound

HRID 1250262Notes

Reaction equation

HRID 1250262 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[N:5]([CH3:7])[CH3:6].[CH3:11][CH:12]([OH:16])[CH2:13][CH:14]=[CH2:15].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>C(N(CC)CC)C.C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:6][N:5]([CH3:7])[C:4]1[CH:3]=[C:2](/[CH:15]=[CH:14]/[CH2:13][CH:12]([OH:16])[CH3:11])[CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 962WaterHCID 122474-Penten-2-OLHCID 80271Tri-o-tolylphosphineHCID 1401023-Bromo-N,N-dimethylaniline

Product 1

HCID 18327739HCID 18327739, compoundYield 63.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 3-bromo-N,N-dimethylaniline (1.00 g, 5.00 mmol), 4-penten-2-ol (450 mg, 5.23 mmol), palladium(II) acetate (11 mg, 0.050 mmol) and tri-o-tolylphosphine (61 mg, 0.20 mmol) was diluted with triethylamine (1.5 mL) and acetonitrile (3 mL) and refluxed under nitrogen for 16 h. The mixture was cooled, poured into water (15 mL) and extracted with chloroform (2×15 mL). The chloroform extracts were dried (Na2SO4) and evaporated. The residue was column chromatographed on 35 g of Merck silica gel 60 (70-230 mesh) with 10-20% (v/v) ethyl acetate, 20% (v/v) chloroform in hexane to give 657 mg (63.7% yield) of light yellow oil.

Workup

  1. temperaturerefluxed under nitrogen for 16 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with chloroform (2×15 mL)
  4. dry with materialThe chloroform extracts were dried (Na2SO4)
  5. customevaporated
  6. customchromatographed on 35 g of Merck silica gel 60 (70-230 mesh) with 10-20% (v/v) ethyl acetate, 20% (v/v) chloroform in hexane
  7. customto give 657 mg (63.7% yield) of light yellow oil

Sources & evidence

ORD record
ord-af3c0a95d4054fa59f4e646bef1ee127
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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