Cornforth reagent → (1-Methyl-1H-imidazol-2-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

HRID 2375735ノート

反応式

HRID 2375735 の反応式
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:22][N:23]1[CH:27]=[CH:26][N:25]=[C:24]1[CH:28]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][O:38]2)=[CH:32][CH:31]=1)[OH:29]>C(Cl)Cl>[CH3:22][N:23]1[CH:27]=[CH:26][N:25]=[C:24]1[C:28]([C:30]1[CH:31]=[CH:32][C:33]([O:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][O:38]2)=[CH:34][CH:35]=1)=[O:29]

参加物

4

反応物 2

HCID 2724130Cornforth reagentHCID 59855116(1-Methyl-1H-imidazol-2-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol

生成物 1

HCID 59855132(1-Methyl-1H-imidazol-2-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone収率 76.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Pyridinium dichromate (36 g, 95.7 mmol) was added to a solution of 9.1 (21 g, 72.7 mmol) in DCM (100 mL) at 0° C. in several portions. The mixture was stirred at 0° C. for 1 hour and at room temperature for 6 hours. Silica gel (75 g) was added to the reaction mixture, and the resulting slurry was filtered through a pad of silica gel. The solid was washed with DCM (200 mL). The filtrate was washed with water and saturated brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give an oily residue, which was flash chromatographed (silica gel, 0-30% EtOAc in hexane) to afford ketone 9.2 as yellow solid (16 g). 1H NMR (500 MHz) (CDCl3) δ 8.33-8.35 (m, 2H); 7.10-7.29 (m, 4H); 5.56 (t, J=3.0 Hz, 1H); 4.08 (s, 3H); 3.85-3.90 (m, 1H); 3.61-3.65 (m, 1H); 2.03 (m, 1H); 1.90-1.91 (m, 2H); 1.69-1.74 (m, 2H); 1.61-1.64 (m, 1H).

後処理

  1. additionSilica gel (75 g) was added to the reaction mixture
  2. filtrationthe resulting slurry was filtered through a pad of silica gel
  3. washThe solid was washed with DCM (200 mL)
  4. washThe filtrate was washed with water and saturated brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give an oily residue, which
  9. customchromatographed (silica gel, 0-30% EtOAc in hexane)

出典と根拠

ORDレコード
ord-b3b8768fac2b468887f54248af980312
出典データセット
uspto-grants-2008_12
特許番号
US07465804B2

反応ノート

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