HCID 22282440, compound → HCID 22282423, compound

HRID 1062659Notes

Reaction equation

HRID 1062659 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([OH:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([C:3]1[CH:4]=[C:5]([C:9](=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 1

HCID 22282440HCID 22282440, compound

Product 1

HCID 22282423HCID 22282423, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 3-(3-cyanophenyl)-3-hydroxypropionate (2.22 g, 10.8 mmol) in 30 mL of methylene chloride was added activated manganese dioxide (4.7 g, 54.0 mmol). This mixture was allowed to stir at 25° C. for 16 h. The reaction mixture was filtered through a pad of celite and concentrated in vacuo. The residue was purified by flash chromatography (elution with 2:1 hexanes/ethyl acetate) to afford 0.9 g (41%) of the title compound along with 0.8 g (36%) of recovered starting material. MS for title compound (H2O GC-MS) 204 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography (elution with 2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-5fbf01ca78324baca3cba5799e4be2a1
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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