海萝胶 → 2-Chloro-1-(oxolan-3-yl)ethanone

HRID 376577

反应方程式

HRID 376577 反应方程式
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.C(Cl)(=O)[C:10]([Cl:12])=O.[N+](=C)=[N-].Cl>ClCCl.CCOCC>[Cl:12][CH2:10][C:6]([CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:8]

参与物

7

反应物 4

HCID 313海萝胶HCID 9550重氮甲烷HCID 65578草酰氯HCID 46613173-四氢呋喃甲酸

产物 1

HCID 187800522-Chloro-1-(oxolan-3-yl)ethanone收率 88.1%

试剂、催化剂与溶剂 2

HCID 3283乙醚溶剂HCID 6344二氯甲烷溶剂2 次

实验过程

(RS)-3-Tetrahydrofuroic acid (3.48g) in dichloromethane (40ml) was treated with oxalyl chloride (11.43g) as described in Example 1(a). The resultant acid chloride in dichloromethane (40ml) was then treated with excess diazomethane (60mM) in ether (100ml), followed by hydrogen chloride. The solution was washed once with brine, dried and concentrated. Flash chromatography on silica gel, eluting with 40% ethyl acetate/hexane afforded the title compound as a pale yellow oil, (3.924g, 88%); vmax (CH2Cl2) 1735 and 1716cm-1 ; 2.17 (2H, dt, J 7.0, 7.5Hz), 3.47-3.58 (1H, m), 3.77-4.04 (4H, m) and 4.18 (2H, s); [mass spectrum: +ve ion (ammonia) MNH4+ (166)].

后处理

  1. washThe solution was washed once with brine
  2. customdried
  3. concentrationconcentrated
  4. washFlash chromatography on silica gel, eluting with 40% ethyl acetate/hexane

来源与证据

ORD记录
ord-6078964c5528424784040ce3217f6797
来源数据集
uspto-grants-2000_02
专利号
US06020329

关联笔记

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