Cerium(III) chloride → HCID 59779138, compound

HRID 1096729Notes

Reaction equation

HRID 1096729 reaction equation
[C:1]1([C:11]2[CH2:15][CH2:14][C:13](=[O:16])[CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Ce+3].[BH4-].[Na+]>C(O)C>[C:1]1([C:11]2[CH2:15][CH2:14][CH:13]([OH:16])[CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 59779163HCID 59779163, compound

Product 1

HCID 59779138HCID 59779138, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3-napthalen-1-yl-cyclopent-2-enone (3.36 g, 16.13 mmol) in ethanol (150 mL) was added cerium trichloride (3.98 g, 16.13 mmol) followed portion-wise by sodium borohydride (0.73 g, 19.36 mmol, 1.2 eq.) at room temperature. The reaction mixture was stirred for 0.5 h, until the reaction was shown to be complete by TLC. The reaction was quenched by the addition of saturated aqueous ammonium chloride (100 mL) and the organics were removed in vacuo. The remaining aqueous layer was further diluted with water (100 mL) and extracted with dichloromethane (3×200 mL). The organic extracts were combined, dried over magnesium sulphate and concentrated in vacuo. The crude oil was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 20%:80%) to afford the desired compound as a yellow oil (2.49 g, 74%). 1H NMR (400 MHz, CDCl3) δ ppm 2.01-2.04 (1H, m, CH), 2.44-2.45 (1H, m, CH), 2.77-2.78 (1H, m, CH), 2.93-2.95 (1H, m, CH), 3.60 (1H, q, J 1.3 Hz, CH), 6.07 (1H, q, J 1.3 Hz, CH), 7.24-7.35 (4H, m, ArH), 7.75 (1H, d, J 8.0 Hz, ArH), 7.78 (1H, d, J 8.0 Hz, ArH), 8.15 (1H, d, J 8.0 Hz, ArH).

Workup

  1. customat room temperature
  2. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride (100 mL)
  3. customthe organics were removed in vacuo
  4. additionThe remaining aqueous layer was further diluted with water (100 mL)
  5. extractionextracted with dichloromethane (3×200 mL)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude oil was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 20%:80%)

Sources & evidence

ORD record
ord-dddd18ef46824eaa93b32cd0b2506f5f
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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