Diisopropylethylamine → HCID 20092833、化合物

HRID 1708420ノート

反応式

HRID 1708420 の反応式
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:12]([C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1)#[N:13].[Br-].[Li+].C(N(C(C)C)CC)(C)C>O1CCCC1.O>[C:12]([C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]1[CH:26]=[CH:25][C:22]([CH2:23][CH:3]([C:2](=[O:1])[CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:21][CH:20]=1)#[N:13]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 82050Lithium BromideHCID 238498Ethyl 3-oxohexanoateHCID 200928574-(3-Cyano-2-thienyl)benzyl bromide

生成物 1

HCID 20092833HCID 20092833、化合物収率 99.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

11 g of ethyl 3-oxohexanoate are dissolved in 150 ml of tetrahydrofuran. 12.9 g of 4-(3-cyano-2-thienyl)benzyl bromide and 6.1 g of lithium bromide are added and the mixture is stirred at room temperature. 24.2 ml of diisopropylethylamine are then added dropwise. After the addition is complete, the reaction mixture is brought to reflux for 24 hours. After evaporation under vacuum, the residue obtained is taken up with water and then extracted with chloroform. The organic phase is dried and then evaporated under vacuum. The excess ethyl 3-oxohexanoate is removed using a vane pump. 16.4 g of ethyl 2-[4-(3-cyano-2-thienyl)benzyl]-3-oxohexanoate are thereby obtained in the form of a pale yellow oil, which is used without further purification for the next step.

後処理

  1. additionAfter the addition
  2. temperatureto reflux for 24 hours
  3. customAfter evaporation under vacuum
  4. customthe residue obtained
  5. extractionextracted with chloroform
  6. customThe organic phase is dried
  7. customevaporated under vacuum
  8. customThe excess ethyl 3-oxohexanoate is removed

出典と根拠

ORDレコード
ord-32a753fc1d9346d9b8101f2475a46e32
出典データセット
uspto-grants-1994_10
特許番号
US05358950

反応ノート

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