聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → (S)-3-羟基四氢呋喃对甲苯磺酸酯

HRID 41231

反应方程式

HRID 41231 反应方程式
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.N1C=CC=CC=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>CCCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[O:4]1[CH2:5][CH2:6][CH:2]([O:1][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH2:3]1

参与物

7

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 1049吡啶HCID 7397对甲苯磺酰氯HCID 99603-羟基四氢呋喃

产物 1

HCID 13837325(S)-3-羟基四氢呋喃对甲苯磺酸酯收率 67.5%

试剂、催化剂与溶剂 2

HCID 8857乙酸乙酯溶剂HCID 21899848Ethylacetate heptane溶剂

实验过程

To a mixture of 3-hydroxytetrahydrofuran (7.00 g, 79.5 mmol) and pyridine (100 mL), was added p-toluenesulfonyl chloride (18.2 g, 95.4 mmol) while stirring at room temperature, and the resulting mixture was stirred for 8.5 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 then the solvent in the filtrate was 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=4/1) to obtain the title compound (13.0 g, 53.7 mmol).

后处理

  1. stirringthe resulting mixture was stirred for 8.5 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 distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

来源与证据

ORD记录
ord-872bb89e4f994941b3711d549ccabc83
来源数据集
uspto-grants-2013_09
专利号
US08530504B2

关联笔记

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