Cerium(III) chloride → 3-Naphthalen-2-yl-cyclopent-2-enol

HRID 1096739Notes

Reaction equation

HRID 1096739 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]=1.[Cl-].[Cl-].[Cl-].[Ce+3].[BH4-].[Na+]>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:15][CH2:14][CH:13]([OH:16])[CH:12]=1

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 597791363-Naphthalen-2-yl-cyclopent-2-enone

Product 1

HCID 597791273-Naphthalen-2-yl-cyclopent-2-enol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(naphthalen-2-yl)cyclopent-2-enone (2.22 g, 10.7 mmol) in ethanol (250 mL) was treated with cerium trichloride (2.63 g, 10.7 mmol, 1 eq.) followed portion wise by sodium borohydride (0.48 g, 12.8 mmol, 1.2 eq.) at room temperature. The reaction mixture was stirred for 0.5 h, then quenched with saturated aqueous ammonium chloride (125 mL) and concentrated to remove ethanol. The concentrate was diluted with water (125 mL) and extracted with dichloromethane (3×125 mL). The combined organic extracts were dried over magnesium sulphate, filtered, and concentrated in vacuo to afford in a quantitative yield as a white solid which was not further purified. 1H NMR (400 MHz, CDCl3) δ ppm 1.89-1.97 (1H, m, CH), 2.48-2.57 (1H, m, CH), 2.75-2.83 (1H, m, CH), 3.00-3.09 (1H, m, CH), 3.27 (1H, q, J 1.3 Hz, CH), 5.04-5.09 (1H, m, OH), 6.36 (1H, q, J 1.9 Hz, CH), 7.39-7.50 (2H, m ArH), 7.70 (1H, dd, J 1.6, 8.5 Hz, ArH), 7.75-7.88 (3H, m, ArH), 7.99 (1H, s, ArH).

Workup

  1. customat room temperature
  2. customquenched with saturated aqueous ammonium chloride (125 mL)
  3. concentrationconcentrated
  4. customto remove ethanol
  5. additionThe concentrate was diluted with water (125 mL)
  6. extractionextracted with dichloromethane (3×125 mL)
  7. dry with materialThe combined organic extracts were dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto afford in a quantitative yield as a white solid which

Sources & evidence

ORD record
ord-da53b828d1a348f8a7811f4e131d4e46
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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