Diphenyl Ether → methyl 6-chloro-5-acetamido-2H-chromene-8-carboxylate

HRID 865395ノート

反応式

HRID 865395 の反応式
[C:1]([NH:4][C:5]1[C:14]([Cl:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:16][CH2:17][C:18]#[CH:19])[CH:6]=1)(=[O:3])[CH3:2].O(C1C=CC=CC=1)C1C=CC=CC=1>>[C:1]([NH:4][C:5]1[C:6]2[CH:19]=[CH:18][CH2:17][O:16][C:7]=2[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][C:14]=1[Cl:15])(=[O:3])[CH3:2]

参加物

3

反応物 2

HCID 7583Diphenyl EtherHCID 10588933Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate

生成物 1

HCID 54402287methyl 6-chloro-5-acetamido-2H-chromene-8-carboxylate収率 33.8%

反応条件

温度
230 °C

実験手順

A mixture of 40 parts of methyl 4-(acetylamino)-5-chloro-2-(2-propynoxy)benzoate and 172 parts of phenoxybenzene was stirred for 45 min. at 230° C. After cooling, the reaction mixture was poured into petroleumether. The organic layer was separated, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2C2 /CH3OH 97:3). The eluent of the desired fractions was evaporated and the residue was crystallized from acetonitrile, yielding 11.9 parts (33.8%) of methyl 5-(acetylamino)-6-chloro-2H-1-benzopyran-8-carboxylate (interm. 11).

後処理

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into petroleumether
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH2C2 /CH3OH 97:3)
  8. customThe eluent of the desired fractions was evaporated
  9. customthe residue was crystallized from acetonitrile

出典と根拠

ORDレコード
ord-34246d5083414210b130cbf1c5c9e24a
出典データセット
uspto-grants-1996_10
特許番号
US05565582

反応ノート

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