Methanol → HCID 68752580、化合物

HRID 588984ノート

反応式

HRID 588984 の反応式
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]

参加物

6

反応物 4

HCID 887MethanolHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 67026987HCID 67026987、化合物

生成物 1

HCID 68752580HCID 68752580、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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 aqueous 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).

後処理

  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 aqueous 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)

出典と根拠

ORDレコード
ord-139ab992256f48ef8563f6d6ec674ca2
出典データセット
uspto-grants-2016_01
特許番号
US09227973B2

反応ノート

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