Pyridine → 2-Methoxypropyl 4-methylbenzenesulfonate

HRID 41234

反応式

HRID 41234 の反応式
ClCCl.[CH3:4][O:5][CH:6]([CH3:9])[CH2:7][OH:8].N1C=CC=CC=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CCCCCCC.C(OCC)(=O)C.C(OCC)(=O)C.O>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:8][CH2:7][CH:6]([O:5][CH3:4])[CH3:9])(=[O:24])=[O:23])=[CH:18][CH:17]=1

参加物

8

反応物 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 148462-Methoxy-1-propanol

生成物 1

HCID 138965262-Methoxypropyl 4-methylbenzenesulfonate収率 71.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 21899848Ethylacetate heptane溶媒

実験手順

To dichloromethane (30 mL) mixture of 2-methoxypropan-1-ol (1.6 g, 17.8 mmol) and pyridine (20.0 mL), was added p-toluenesulfonyl chloride (4.07 g, 21.4 mmol) while stirring on ice, and the mixture was stirred at room temperature for five hours. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=2/1) to obtain the title compound (3.12 g, 12.8 mmol).

後処理

  1. stirringthe mixture was stirred at room temperature for five hours
  2. stirringAfter thoroughly shaking the mixture
  3. customthe organic layer was separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe mixture was filtered
  7. distillationthe solvent in the filtrate was then distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

出典と根拠

ORDレコード
ord-a871361464a84328b4e7488902f129ec
出典データセット
uspto-grants-2013_09
特許番号
US08530504B2

関連ノート

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