Cerium(III) chloride → HCID 54032203, compound

HRID 1418772Notes

Reaction equation

HRID 1418772 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[CH2:5]([Li])[CH2:6][CH2:7][CH3:8].[CH3:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([CH3:19])[C:12]=1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([CH:30]([CH3:32])[CH3:31])[CH:23]=1)=[O:21].[NH4+].[Cl-]>O1CCCC1>[CH3:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([CH3:19])[C:12]=1[C:20]([C:22]1[C:27]([CH2:5][CH2:6][CH2:7][CH3:8])=[CH:26][C:25]([O:28][CH3:29])=[C:24]([CH:30]([CH3:32])[CH3:31])[CH:23]=1)=[O:21]

Participants

6

Reactant 4

HCID 24636Cerium(III) chlorideHCID 25517Ammonium ChlorideHCID 57170851HCID 57170851, compoundHCID 178418339Butyllithium

Product 1

HCID 54032203HCID 54032203, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To anhydrous cerium chloride (3.16 g, 12.8 mmol) dry tetrahydrofuran (50 mL) was added with stirring under argon and stirring was continued for 2 hours at room temperature. The resultant suspension was then cooled to -78° C., and 6.4 mL of n-butyllithium (2.0M in pentane) was added with stirring, whereupon the color of the suspension turned from white to yellow. After maintaining the same temperature for 30 minutes, (2,6-dimethyl-4-methoxyphenyl)-(3-isopropyl-4-methoxyphenyl) methanone (10) (1 g, 3.20 mmol) in tetrahydrofuran (5 mL) was added and the mixture was stirred for 3 hours at -78° C. and for 2 hours at 0° C. The reaction mixture was treated with sat. NH4Cl solution, filtered through Celite, and extracted with ethyl acetate. The combined extracts were dried (Na2SO4), evaporated, and the residue was purified by flash column chromatography (silica gel, 95:5 hexane/ethylacetate) to give (2,6-dimethyl-4-methoxyphenyl)-(6-n-butyl-3-isopropyl-4-methoxyphenyl) methanone (15) (500 mg, 43%); 1HNMR (CDCl3) δ 0.98 (t, 3H), 1.03 (d, 6H), 1.41 (m, 2H), 1.59 (m, 2H), 2.09 (s, 6H), 3.05 (t, 2H), 3.14 (heptet, 1H),3.86 (d, 6H), 6.52 (d, 2H), 6.73 (s, 2H), 7.22 (s, 1H).

Workup

  1. stirringstirring
  2. stirringwith stirring, whereupon the color of the suspension
  3. temperatureAfter maintaining the same temperature for 30 minutes
  4. stirringthe mixture was stirred for 3 hours at -78° C. and for 2 hours at 0° C
  5. filtrationfiltered through Celite
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined extracts were dried (Na2SO4)
  8. customevaporated
  9. customthe residue was purified by flash column chromatography (silica gel, 95:5 hexane/ethylacetate)

Sources & evidence

ORD record
ord-876c9244c80f4c16bf9770905024386a
Source dataset
uspto-grants-1999_03
Patent number
US05883294

Reaction notes

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