Methanol → HCID 68752580, 화합물

HRID 1404477노트

반응식

HRID 1404477 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 68752580HCID 68752580, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cfa78321a4854c4d95126f32f00bf17a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912210B2

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