Tetrahydro-4H-pyran-4-one → HCID 43608624, compound

HRID 2401677Notes

Reaction equation

HRID 2401677 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([Cl:9])[CH:3]=1.[O:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:13]2[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)=[C:4]([Cl:9])[CH:3]=1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 6101694-Bromo-2-chloroanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43608624HCID 43608624, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-bromo-2-chloro-phenylamine (4 g, 19.37 mmol), tetrahydro-4H-pyran-4-one (2.69 ml, 29.05 mmol), oven dried molecular sieves 4 Å (2 g) and sodium triacetoxyborohydride (6.12 g, 29.05 mmol) in 1,2-dichloroethane (100 ml) was stirred at room temperature for 72 hours. The mixture was filtered through a diatomaceous earth pad. The diatomaceous earth pad was washed with dichloromethane. The combined filtrates were washed with NaHCO3 (aqueous saturated solution), dried over Na2SO4 and evaporated till dryness. The crude product thus obtained was purified by column chromatography (silica gel; DCM to DCM/MeOH(NH3) up to 5%). The desired fractions were collected and evaporated in vacuo to yield intermediate 12 as a brown oil (4.83 g, 86%).

Workup

  1. filtrationThe mixture was filtered through a diatomaceous earth pad
  2. washThe diatomaceous earth pad was washed with dichloromethane
  3. washThe combined filtrates were washed with NaHCO3 (aqueous saturated solution)
  4. dry with materialdried over Na2SO4
  5. customevaporated till dryness
  6. customThe crude product thus obtained
  7. customwas purified by column chromatography (silica gel
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-28d67af522f44e1bbb55e57b4860c441
Source dataset
uspto-grants-2014_08
Patent number
US08796311B2

Reaction notes

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