Potassium Hydroxide → HCID 20032358、化合物

HRID 231451ノート

反応式

HRID 231451 の反応式
[CH3:1][O:2][NH:3][C:4](=[O:6])[CH3:5].[OH-].[K+].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[C:12]([Cl:18])[CH:11]=1>O1CCCC1.C(OCC)C.C1OCCOCCOCCOCCOCCOC1>[Cl:18][C:12]1[CH:11]=[C:10]([F:9])[CH:17]=[CH:16][C:13]=1[CH2:14][N:3]([O:2][CH3:1])[C:4](=[O:6])[CH3:5]

参加物

7

反応物 3

HCID 14797Potassium HydroxideHCID 138591N-MethoxyacetamideHCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzene

生成物 1

HCID 20032358HCID 20032358、化合物収率 33.5%

試薬・触媒・溶媒 3

HCID 2855718-Crown-6触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred mixture of 1.95 g (0.0219 mole) of N-methoxyacetamide, 1.23 g 0.022 mole) of powdered potassium hydroxide, and a small amount (~0.05 g) of 18-crown-6 in 10 ml of tetrahydrofuran was added a solution of 5.05 g (0.0226 mole) of 4-fluoro-2-chlorobenzyl bromide in 15 ml of tetrahydrofuran. This mixture was heated at reflux for approximately 17 hours and then was allowed to cool to room temperature. The mixture was diluted with 125 ml of diethyl ether and was washed with an aqueous, saturated sodium chloride solution. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving a yellow oil. This oil was purified by column chromatography on silica gel, eluting with ethyl acetate:n-heptane (25:75) followed by ethyl acetate:n-heptane (50:50) , to yield 1.7 g of N-(2-chloro-4-fluoro-benzyl)-N-methoxyacetamide as an oil.

後処理

  1. temperatureThis mixture was heated
  2. temperatureat reflux for approximately 17 hours
  3. washwas washed with an aqueous, saturated sodium chloride solution
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customleaving a yellow oil
  8. customThis oil was purified by column chromatography on silica gel
  9. washeluting with ethyl acetate:n-heptane (25:75)

出典と根拠

ORDレコード
ord-0762b866d1654bfe961474f9b99ac86b
出典データセット
uspto-grants-1989_07
特許番号
US04846882

反応ノート

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