四氢呋喃 → Methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate

HRID 1697

反应方程式

HRID 1697 反应方程式
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:33](=[C:36]1[CH:41]=C(O)C=CO1)(=[O:35])=[O:34].N(C(OCC)=O)=NC(OCC)=[O:46].[CH2:55]1[CH2:59][O:58][CH2:57][CH2:56]1>>[S:33](=[C:36]1[CH:55]=[CH:59][O:58][C:57]([C:56]([O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=2)=[O:46])=[CH:41]1)(=[O:35])=[O:34]

参与物

6

反应物 5

HCID 8028四氢呋喃2 次HCID 11776三苯基膦HCID 220568偶氮二甲酸二乙酯HCID 125326764-羟基-2-甲基氧苯甲酸甲酯HCID 19690976Sulfonylpyran-4-ol

产物 1

HCID 86752226Methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate

反应条件

温度
0 °C

实验过程

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (364 mg, 2.0 mmol) in dry THF (4 mL) was added triphenylphosphine (524.6 mg, 2.0 mmol) and the solution was cooled to 0° C. A 2.5 mL volume of sulfonylpyran-4-ol (200 mg, 1.33 mmol) and diethyl azodicarboxylate (315 μL, 2.0 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 60:40 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate.

后处理

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was chromatographed on a silica gel column
  4. washEtOAc and eluted with same
  5. customthe solvent removed under reduced pressure

来源与证据

ORD记录
ord-e3ff06e7d5dc4790a4038ff5d1f041f4
来源数据集
uspto-grants-1998_03
专利号
US05726172

关联笔记

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