Methanol → HCID 68752580, compound

HRID 1404477Notes

Reaction equation

HRID 1404477 reaction equation
C([C:3]1[CH:4]=[C:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[N:7][C:8]=1[CH:9]=C)=C.[O:18]=[O+][O-].[BH4-].[Na+].[CH3:23][OH:24]>ClCCl>[OH:24][CH2:23][C:3]1[CH:4]=[C:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[N:7][C:8]=1[CH2:9][OH:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 67026987HCID 67026987, compound

Product 1

HCID 68752580HCID 68752580, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5,6-diethenylpyridine-3-carboxylate (19.0 g, 82 mmol) in dichloromethane (821 mL) at −78° C. was added ozone gas. The ozone bubbled though the solution until saturated (1 h). Nitrogen gas was then bubbled through the solution. The mixture was diluted with methanol (821 mL) and sodium borohydride (7.77 g, 205 mmol) was added. After 15 min, the mixture was quenched with saturated aqeuous sodium bicarbonate and washed with dichloromethane (3×). The combined organics were washed with brine, dried with magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→15% methanol/dichloromethane) gave the title compound. MS: m/z=240.3 (M+1).

Workup

  1. customThe ozone bubbled though the solution until saturated (1 h)
  2. customNitrogen gas was then bubbled through the solution
  3. additionwas added
  4. customthe mixture was quenched with saturated aqeuous sodium bicarbonate
  5. washwashed with dichloromethane (3×)
  6. washThe combined organics were washed with brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel chromatography (100% dichloromethane→15% methanol/dichloromethane)

Sources & evidence

ORD record
ord-cfa78321a4854c4d95126f32f00bf17a
Source dataset
uspto-grants-2014_12
Patent number
US08912210B2

Reaction notes

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