Sodium borohydride → HCID 59779154, compound

HRID 1096705Notes

Reaction equation

HRID 1096705 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2[CH2:11][CH2:10][C:9](=[O:12])[CH:8]=2)=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([C:7]2[CH2:11][CH2:10][CH:9]([OH:12])[CH:8]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11008393HCID 11008393, compound

Product 1

HCID 59779154HCID 59779154, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-p-tolyl-cyclopent-2-en-1-one (5.0 g, 29.07 mmol) in ethanol (100 mL) was treated with CeCl3 (7.15 g, 29.07 mmol) followed portionwise by NaBH4 (1.32 g, 34.9 mmol) at room temperature. The reaction mixture was stirred for 0.5 h, then quenched with saturated aqueous NH4Cl and concentrated to remove ethanol. The concentrate was diluted with H2O and extracted with DCM (3×). The combined organic extracts were dried over MgSO4, filtered, concentrated in vacuo and purified by silica gel chromatography using 10-30% EtOAc/Heptane as the eluting solvent to afford 3.8 g (Yield 75%) of 3-p-tolyl-cyclopent-2-en-1-ol. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15-1.31 (m, 1 H) 1.55-1.73 (m, 1 H) 2.17-2.26 (m, 1 H) 2.22-2.32 (m, 3 H) 2.41-2.54 (m, 1 H) 2.66-2.78 (m, 1 H) 4.72 (d, 1 H) 4.74-4.80 (m, 1 H) 6.12-6.17 (m, 1 H) 7.13 (d, 2 H) 7.36 (d, 2 H)

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. concentrationconcentrated
  3. customto remove ethanol
  4. additionThe concentrate was diluted with H2O
  5. extractionextracted with DCM (3×)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-4ebaf6c805324c83b453173810f9d4c7
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

Loading…