Acetone → 9-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester

HRID 575050

反応式

HRID 575050 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[C:8](Br)(Br)[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=[O:4].CC(C)=[O:24]>O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[C:8](=[O:24])[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=[O:4]

参加物

4

反応物 2

HCID 180AcetoneHCID 866930864,4,9-Tribromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester

生成物 1

HCID 866930859-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester収率 86%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

The mixture of 4,4,9-Tribromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (9.0 g, 18.07 mmol) in acetone (250 mL) and water (250 mL) was stirred at room temperature for 4 h. Then the mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×200 mL). The combined organic layers were washed with brine, dried over Na2SO4, concentrated to afford the crude product which was triturated with EtOAc and hexane (EtOAc/hexane=1/5). After filtration, the solid was dried in vacuo to afford compound 9-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (5.5 g, 86%) as a light yellow solid.

後処理

  1. customThen the mixture was partitioned between EtOAc and H2O
  2. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto afford the crude product which
  7. customwas triturated with EtOAc and hexane (EtOAc/hexane=1/5)
  8. filtrationAfter filtration
  9. customthe solid was dried in vacuo

出典と根拠

ORDレコード
ord-1fde194404a645fa8a9a098b5bdb15d2
出典データセット
uspto-grants-2015_05
特許番号
US09034866B2

関連ノート

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