海萝胶 → (2-methyl-5-phenylfuran-3-yl)(tetrahydro-2H-pyran-4-yl)methanol

HRID 1877035

反应方程式

HRID 1877035 反应方程式
[CH3:1][C:2]1[O:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH:7]=[O:8].Br[Mg][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C(OCC)C.Cl.O>O1CCCC1>[CH3:1][C:2]1[O:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH:7]([CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[OH:8]

参与物

6

反应物 4

HCID 313海萝胶HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 27953132-Methyl-5-phenyl-3-furaldehydeHCID 178467675HCID 178467675，化合物

产物 1

HCID 68514112(2-methyl-5-phenylfuran-3-yl)(tetrahydro-2H-pyran-4-yl)methanol收率 86%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
0 °C

实验过程

To a solution of 2-methyl-5-phenylfuran-3-carbaldehyde (1.9 g) in tetrahydrofuran (30 mL) was added dropwise bromo(tetrahydro-2H-pyran-4-yl)magnesium-diethyl ether solution (30 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 30 min. The reaction mixture was treated with 1N hydrochloric acid, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (10% ethyl acetate/hexane to 40% ethyl acetate/hexane) to give the title compound (2.3 g, 86%) as an oil.

后处理

  1. additionafter the completion of the dropwise addition
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column (10% ethyl acetate/hexane to 40% ethyl acetate/hexane)

来源与证据

ORD记录
ord-9ee7c736d71249d8b6d97a2b035b8719
来源数据集
uspto-grants-2012_11
专利号
US08309580B2

关联笔记

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