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Dimethylformamide → methyl 7-tert-butylcarbonylamino-4-chloro-3-formyl-2H-chromene-8-carboxylate

HRID 1778392
ノート
印刷プレビュー

反応式

HRID 1778392 の反応式
[C:1]([C:5]([NH:7][C:8]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]2[C:11]([C:12](=O)[CH2:13][CH2:14][O:15]2)=[CH:10][CH:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].CN([CH:26]=[O:27])C.P(Cl)(Cl)([Cl:30])=O>ClC=C(Cl)Cl.C(Cl)Cl>[C:1]([C:5]([NH:7][C:8]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]2[C:11]([C:12]([Cl:30])=[C:13]([CH:26]=[O:27])[CH2:14][O:15]2)=[CH:10][CH:9]=1)=[O:6])([CH3:2])([CH3:3])[CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychloride2 回HCID 66693192Methyl 7-tert-butylcarbonylamino-4-oxochroman-8-carboxylate2 回

生成物 1

HCID 86684737methyl 7-tert-butylcarbonylamino-4-chloro-3-formyl-2H-chromene-8-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 6575
Trichloroethylene
溶媒

反応条件

温度
60 °C

実験手順

A suspension of methyl 7-tert-butylcarbonylamino-4-oxochroman-8-carboxylate (Intermediate 77, 1.32 g) in trichloroethylene (25 mL) was treated with DMF (1.5 mL), followed by dropwise addition of phosphorus oxychloride (0.998 g). The resultant mixture was heated at 60° C. for 2 hours. A further amount of phosphorus oxychloride (0.200 g) was added and the mixture was heated at 60° C. for 40 minutes. After cooling, the mixture was diluted with DCM and washed with saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted with DCM and the combined organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-25% to give methyl 7-tert-butylcarbonylamino-4-chloro-3-formyl-2H-chromene-8-carboxylate (1.175 g) as a yellow solid.

後処理

  1. temperatureAfter cooling
  2. washwashed with saturated aqueous sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted with DCM
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-25%

出典と根拠

ORDレコード
ord-e078fc4cc76940f58b34499b6204e383
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266896B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート