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Diisopropylamine → HCID 21929097、化合物

HRID 1243848
ノート
印刷プレビュー

反応式

HRID 1243848 の反応式
[N+:1](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-:2].[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:21][CH2:20][C:19](=O)[CH:18]=[CH:17]2)=[CH:12][CH:11]=1.C([N-]C(C)C)(C)C.[Li+].C([Li])CCC.C(NC(C)C)(C)C>O1CCCC1.C(OCC)(=O)C.C(O)(=O)C>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[CH2:17][C:18]3[NH:2][N:1]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:19]=3[CH:20]=[CH:21]2)=[CH:14][CH:15]=1
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

9

反応物 5

HCID 7912DiisopropylamineHCID 12192Ethyl diazoacetateHCID 2724682Lithium diisopropylamideHCID 219287994,4-Bis(4-fluorophenyl)cyclohex-2-enoneHCID 178418339Butyllithium

生成物 1

HCID 21929097HCID 21929097、化合物

試薬・触媒・溶媒 3

HCID 176
Acetic Acid
溶媒
HCID 8028Tetrahydrofuran溶媒2 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
-70 °C

実験手順

1.4 cm3 of ethyl diazoacetate are added dropwise to a solution, cooled to −70° C., of 3 g of 4,4-bis(4-fluorophenyl)cyclohex-2-enone in 75 cm3 of tetrahydrofuran, followed by slow addition of 37.9 cm3 of lithium diisopropylamide solution prepared from 10.5 cm3 of 1.6 M n-butyllithium and 2.4 cm3 of diisopropylamine in solution in 25 cm3 of tetrahydrofuran. After stirring the reaction mixture at a temperature in the region of −70° C. for 3 hours, 1.9 cm3 of glacial acetic acid are added and the temperature is allowed to rise to the region of 20° C. 250 cm3 of ethyl acetate are added and the organic phases are then washed with twice 150 cm3 of distilled water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue is dissolved in 100 cm3 of toluene and heated at a temperature in the region of 110° C. for 3 hours and then concentrated to dryness under reduced pressure. The residue obtained is purified by flash chromatography on silica gel (35–70 μm), eluting with a dichloromethane/diisopropyl ether (50/50) mixture; 1.2 g of ethyl 6,6-bis(4-fluorophenyl)-6,7-dihydro-1H-indazole-3-carboxylate are thus obtained in the form of a beige-coloured foam, the characteristics of which are as follows:

後処理

  1. customto rise to the region of 20° C
  2. washthe organic phases are then washed with twice 150 cm3 of distilled water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated to dryness under reduced pressure
  5. dissolutionThe residue is dissolved in 100 cm3 of toluene
  6. temperatureheated at a temperature in the region of 110° C. for 3 hours
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue obtained
  9. customis purified by flash chromatography on silica gel (35–70 μm)
  10. washeluting with a dichloromethane/diisopropyl ether (50/50) mixture

出典と根拠

ORDレコード
ord-ee0e9e58265a4df2965332d240eee2c5
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07119115B2

反応ノート

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