N,N-二甲基甲酰胺 → HCID 10805854，化合物

HRID 1069652笔记

反应方程式

HRID 1069652 反应方程式
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][CH:7]=1)[CH3:2].CN(C=O)C.[H-].[Na+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:7]=1)[CH3:2]

参与物

8

反应物 4

HCID 6228N,N-二甲基甲酰胺HCID 7498溴化苄HCID 24758氢化钠HCID 105138022-(5-甲氧基-1H-吲哚-3-基)乙酸乙酯

产物 1

HCID 10805854HCID 10805854，化合物收率 82%

试剂、催化剂与溶剂 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8028四氢呋喃溶剂HCID 8857乙酸乙酯溶剂

实验过程

5-Methoxy-1H-indole-3-acetic acid ethyl ester (10.1 g, 41 mmol) was dissolved in 50 mL of THF and 200 mL of DMF and 1.8 g (45 mmol) of 60% NaH/mineral oil were added in portions with cooling. After 0.17 hours, 5 mL (42 mmol) of benzyl bromide was added and stirring maintained for 1.5 hours. The mixture was diluted with water and ethyl acetate, the organic layer separated, washed with water, brine and dried (Na2SO4). The solution was evaporated at reduced pressure and the residue chromatographed on silica gel eluting with a gradient, 25% ethyl acetate/hexane→40% ethyl acetate/hexane, to give 10.8 g (82% yield) of 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester.

后处理

  1. temperaturewith cooling
  2. temperaturemaintained for 1.5 hours
  3. customthe organic layer separated
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customThe solution was evaporated at reduced pressure
  7. customthe residue chromatographed on silica gel eluting with a gradient, 25% ethyl acetate/hexane→40% ethyl acetate/hexane

来源与证据

ORD记录
ord-568b0a439dba470d8a06677c45589ceb
来源数据集
uspto-grants-2001_06
专利号
US06252084B1

反应笔记

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