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Triethylamine → Methyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole-4-carboxylate

HRID 1689819
ノート
印刷プレビュー

反応式

HRID 1689819 の反応式
C(N(CC)CC)C.[CH3:8][O:9][C:10](=[O:17])[CH2:11][C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13].ClO[N:20]=[CH:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29]>CCO.CCOC(C)=O>[CH3:8][O:9][C:10]([C:11]1[C:21]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:29])=[N:20][O:13][C:12]=1[CH:14]1[CH2:16][CH2:15]1)=[O:17]
参加物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 8471TriethylamineHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl EsterHCID 866424822,6-Dichloro-benzaldehyde chloro-oxime

生成物 1

HCID 53421832Methyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole-4-carboxylate収率 64%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

Triethylamine (1.82 L, 12.84 mol) is added to 3-cyclopropyl-3-oxo-propionic acid methyl ester (913 g, 6.42 mol) and the mixture is stirred at room temperature for 30 minutes. Then, the mixture is cooled to about 10° C. and a suspension of 2,6-dichloro-benzaldehyde chloro-oxime (1440.9 g, 6.42 mol) in EtOH (3.2 L) is added slowly (the internal temperature does not exceed 24° C.). After the addition, the reaction is stirred overnight at room temperature. The reaction is diluted with EtOAc (5.3 L) and washed with water (1.7 L). The layers are separated and the aqueous layer is extracted with EtOAc (3 L). The combined organics are washed with brine, dried over Na2SO4 (anhyd), filtered and concentrated to about 10% of its total volume. The precipitate formed is filtered, triturated with ether (2 L) and dried under vacuum to obtain title compound (1275.36 g, 64% yield) as a white solid. MS (m/e): 312 (M+1).

後処理

  1. temperatureThen, the mixture is cooled to about 10° C.
  2. additionis added slowly (the internal temperature
  3. customdoes not exceed 24° C.
  4. additionAfter the addition
  5. stirringthe reaction is stirred overnight at room temperature
  6. washwashed with water (1.7 L)
  7. customThe layers are separated
  8. extractionthe aqueous layer is extracted with EtOAc (3 L)
  9. washThe combined organics are washed with brine
  10. dry with materialdried over Na2SO4 (anhyd)
  11. filtrationfiltered
  12. concentrationconcentrated to about 10% of its total volume
  13. customThe precipitate formed
  14. filtrationis filtered
  15. customtriturated with ether (2 L)
  16. customdried under vacuum

出典と根拠

ORDレコード
ord-86627788598c4392949af9c85fdbec25
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08153624B2

反応ノート

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