Pyridine → HCID 86691233, compound

HRID 2038218Notes

Reaction equation

HRID 2038218 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH:8]([OH:12])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8](=[O:12])[CH2:9][O:10][CH3:11])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 86691234HCID 86691234, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86691233HCID 86691233, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 1-(4-fluorophenoxy)-3-methoxy-propan-2-ol (2.6 g, 12.99 mmol) in DCM (26 mL) and add molecular sieves, pyridinium chlorochromate (7.14 g, 32.47 mmol), and pyridine (5.25 mL, 64.93 mmol). Stir the mixture at ambient temperature overnight. Filter the mixture through a Celite® plug and wash the plug with Et2O. Concentrate the filtrate; then purify via flash column chromatography using 25% EtOAc in hexanes to provide the product as a clear oil (872 mg, 33.9%). MS (m/z): 216 (M+NH4).

Workup

  1. filtrationFilter the mixture through a Celite® plug
  2. washwash the plug with Et2O
  3. concentrationConcentrate the filtrate
  4. customthen purify via flash column chromatography

Sources & evidence

ORD record
ord-a2b0649979ed4fc1997ce5da109ec77b
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Reaction notes

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