Cerium(III) chloride → HCID 54537602, compound

HRID 1418768Notes

Reaction equation

HRID 1418768 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[CH3:5][Li].[CH3:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([CH3:16])[C:9]=1[C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH:27]([CH3:29])[CH3:28])[CH:20]=1)=[O:18].[NH4+].[Cl-]>O1CCCC1>[CH3:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([CH3:16])[C:9]=1[C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH:27]([CH3:29])[CH3:28])[CH:20]=1)([OH:18])[CH3:5]

Participants

6

Reactant 4

HCID 24636Cerium(III) chlorideHCID 25517Ammonium ChlorideHCID 57170851HCID 57170851, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 54537602HCID 54537602, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To anhydrous cerium chloride (1.185 g, 4.80 mmol) dry tetrahydrofuran (15 mL) was added with stirring under argon and stirring was continued for 2 hours at room temperature. The resultant suspension was then cooled at -78° C., and 3.43 mL of methyllithium (1.4M in diethylether) 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, 97:3 hexane/ethylacetate) to give 1-(2,6-dimethyl-4-methoxyphenyl)-1-(3-isopropyl-4-methoxyphenyl) ethanol (12) (450 mg, 1.37 mmol, 43%); 1HNMR (CDCl3) δ 1.20 (dd, 6H), 1.58 (s, 3H), 2.12 (s, 3H), 2.18 (s, 3H), 3.30 (heptet, 1H), 3.82 (s, 3H), 3.88 (s, 3H), 6.50 (s, 1H), 6.60 (s, 2H), 6.80 (d, 1H), 7.06 (d, 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, 97:3 hexane/ethylacetate)

Sources & evidence

ORD record
ord-f888ca15cc754f49aa9c89e3f6a966d3
Source dataset
uspto-grants-1999_03
Patent number
US05883294

Reaction notes

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