Ethyl Acetate → (E)-3-(4-iodophenyl)-3-(6-phenylpyridin-3-yl)prop-2-en-1-ol

HRID 549862Notes

Reaction equation

HRID 549862 reaction equation
C[O-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:10]1([C:16]2[N:21]=[CH:20][C:19]([C:22]#[C:23][CH2:24][OH:25])=[CH:18][CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)(=O)C.[I:32][C:33]1[CH:38]=[CH:37][C:36](I)=[CH:35][CH:34]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[I:32][C:33]1[CH:38]=[CH:37][C:36](/[C:22](/[C:19]2[CH:20]=[N:21][C:16]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:17][CH:18]=2)=[CH:23]\[CH2:24][OH:25])=[CH:35][CH:34]=1

Participants

9

Reactant 6

HCID 8857Ethyl AcetateHCID 12208p-DiiodobenzeneHCID 521585Tris(furan-2-yl)phosphaneHCID 10942334Sodium MethoxideHCID 192614273-(6-Phenylpyridin-3-yl)prop-2-yn-1-olHCID 21226445Aluminium lithium hydride

Product 1

HCID 19261803(E)-3-(4-iodophenyl)-3-(6-phenylpyridin-3-yl)prop-2-en-1-ol

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium methoxide (2.5 mg, 0.045 mmol) was added to 1 M solution of lithium aluminum hydride in tetrahydrofuran (1.43 mL, 1.43 mmol). The mixture was cooled to 0° C. and a solution of 3-(6-phenylpyridin-3-yl)prop-2-yn-1-ol (300 mg, 1.43 mmol) in tetrahydrofuran (6 mL) was slowly added. The reaction mixture was stirred at 0° C. for 2 h and then at ambient temperature for 2 h. The reaction mixture was cooled to 0° C. again, ethyl acetate (0.24 mL, 2.4 mmol) was added and the mixture was stirred for further 10 min without cooling. 1,4-Diiodobenzene (527 mg, 1.60 mmol), anhydrous zinc chloride (108 mg, 1.23 mmol), tris(dibenzylideneacetone)dipalladium chloroform complex (29.5 mg, 0.029 mmol) and tri-(2-furyl)phosphine (26.6 mg, 0.118 mmol) were added, the mixture was degassed and kept under argon. The mixture was heated at 60° C. for 20 h; methanol (0.7 mL) was added and the mixture was stirred for additional 1 h. The reaction mixture was diluted with ether (30 mL) and subsequently saturated aqueous solution of ammonium chloride (0.36 mL) was added. The formed suspension was filtered through a paddle of silica gel and the paddle was thoroughly washed with ethyl acetate. The combined filtrates were concentrated in vacuo and the residue was submitted to column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 1:1) affording (E)-3-(4-iodophenyl)-3-(6-phenylpyridin-3-yl)prop-2-en-1-ol.

Workup

  1. waitat ambient temperature for 2 h
  2. temperatureThe reaction mixture was cooled to 0° C. again
  3. stirringthe mixture was stirred for further 10 min
  4. temperaturewithout cooling
  5. customthe mixture was degassed
  6. temperatureThe mixture was heated at 60° C. for 20 h
  7. additionmethanol (0.7 mL) was added
  8. stirringthe mixture was stirred for additional 1 h
  9. additionThe reaction mixture was diluted with ether (30 mL) and subsequently saturated aqueous solution of ammonium chloride (0.36 mL)
  10. additionwas added
  11. filtrationThe formed suspension was filtered through a paddle of silica gel
  12. washthe paddle was thoroughly washed with ethyl acetate
  13. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-d57340a5cdf94983b5639e5003c22d11
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

Loading…