Sulfuric Acid → 1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanone

HRID 898134ノート

反応式

HRID 898134 の反応式
[CH2:1]([S:7][C:8]1[N:13]=[C:12]([CH:14]([OH:16])[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.OS(O)(=O)=O>CC(C)=O>[CH2:1]([S:7][C:8]1[N:13]=[C:12]([C:14](=[O:16])[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 692907201-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanolHCID 131709961Jones' reagent

生成物 1

HCID 692927551-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanone収率 44%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
20 °C

実験手順

1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanol (2.2 g, 8.65 mmol) was dissolved under nitrogen in acetone (20 mL). Then 2 M Jones' reagent prepared from 20 g CrO3 in 100 mL 4 M H2SO4 (6.5 mL, 13 mmol) was add dropwise. After stirring for 2 h at 20° C., the resulting green solution was decanted from the chromium salts and extracted with AcOEt and sat. NaCl solution. The crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient. One obtained 960 mg (44 %) of white crystals. MS: m/z=252 (M).

後処理

  1. additionwas add dropwise
  2. customthe resulting green solution was decanted from the chromium salts
  3. extractionextracted with AcOEt and sat. NaCl solution
  4. customThe crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient

出典と根拠

ORDレコード
ord-203a9b8813974ef6b56ea1e9bbf0b63d
出典データセット
uspto-grants-2008_04
特許番号
US07351700B2

反応ノート

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