Pyridine → HCID 67360689, compound

HRID 404397Notes

Reaction equation

HRID 404397 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([C:18]([OH:20])=[O:19])=[CH:12][C:13]([CH2:16][OH:17])=[CH:14][CH:15]=1.N1C=CC=CC=1.[C:27](Cl)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]>C1COCC1>[CH3:29][C:28]([CH3:31])([CH3:30])[C:27]([O:17][CH2:16][C:13]1[CH:12]=[C:11]([C:18]([OH:20])=[O:19])[C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])=[CH:15][CH:14]=1)=[O:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 57467590HCID 57467590, compound

Product 1

HCID 67360689HCID 67360689, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
12.5 °C

Procedure

To a 0° C. mixture of 29.1 (2.2 g, 7.9 mmol) in THF (20 mL) was added pyridine (1.56 g, 19.8 mmol) followed by pivaloyl chloride (0.96 g, 7.9 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA). The resulting solution was stirred at 0-25° C. overnight and was then quenched with water and treated with 2.0 N HCl (15 mL). The mixture was extracted with EtOAc (3×30 mL). The organic layers were combined and washed with water (10 mL) and brine (10 mL). After removal of organic solvents under reduced pressure, purification of the residue by flash chromatography on silica gel with 0-65% EtOAc/hexanes for elution gave 29.2 as white solid (1.60 g, 56%).

Workup

  1. customwas then quenched with water
  2. additiontreated with 2.0 N HCl (15 mL)
  3. extractionThe mixture was extracted with EtOAc (3×30 mL)
  4. washwashed with water (10 mL) and brine (10 mL)
  5. customAfter removal of organic solvents
  6. customunder reduced pressure, purification of the residue by flash chromatography on silica gel with 0-65% EtOAc/hexanes
  7. washfor elution

Sources & evidence

ORD record
ord-e61d32afcfa341e5887db70e2d37e3c5
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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