Sodium borohydride → HCID 59779123, compound

HRID 1096719Notes

Reaction equation

HRID 1096719 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59779172HCID 59779172, compound

Product 1

HCID 59779123HCID 59779123, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(3,4-dichlorophenyl)cyclopent-2-en-1-one (2 g, 8.8 mmol) in methanol (40 mL) at 0° C. was treated with CeCl3 7H2O (4.26 g, 11.4 mmol) followed portionwise by NaBH4 (0.43 g, 11.4 mmol). The reaction was warmed to room temperature. The reaction mixture was stirred for 4 h, then quenched with saturated aqueous NH4Cl and concentrated to remove methanol. The concentrate was diluted with H2O and extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, concentrated in vacuo and purified by silica gel chromatography using CH2Cl2/Methanol as the eluting solvent to afford 2 g (Yield 99%) of the target compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.82-1.92 (m, 1 H) 2.40-2.52 (m, 1 H) 2.54-2.65 (m, 1 H) 2.79-2.91 (m, 1 H) 4.96-5.04 (m, 1 H) 6.20-6.26 (m, 1 H) 7.27-7.31 (m, 1 H) 7.37-7.42 (m, 1 H) 7.51 (d, 1 H).

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. concentrationconcentrated
  3. customto remove methanol
  4. additionThe concentrate was diluted with H2O
  5. extractionextracted with EtOAc (3×)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-9054b5b9ae04464fa0c76d3d7e6671f5
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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