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4-Benzyloxybenzyl chloride → 2-(2-(4-Benzyloxy-phenyl)-ethyl]-6,7-difluoro-quinoline

HRID 226264
ノート
印刷プレビュー

反応式

HRID 226264 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.C([N-]C(C)C)(C)C.[Li+].[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36]Cl)=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([O:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:36][CH2:13][C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][C:11]([F:12])=[C:2]([F:1])[CH:3]=3)[N:8]=2)=[CH:34][CH:35]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=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

5

反応物 3

HCID 700424-Benzyloxybenzyl chlorideHCID 2724682Lithium diisopropylamideHCID 222413776,7-Difluoro-2-methylquinoline

生成物 1

HCID 577544362-(2-(4-Benzyloxy-phenyl)-ethyl]-6,7-difluoro-quinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

A solution of 8.9 g (49.6 mmol) of the product from Example 1, step 3 in 90 ml THF is cooled at −50° C. 28.6 ml (57.2 mmol) of a 2M solution of lithium diisopropylamide are added and the solution is allowed to heat to −10° C. After 15′ stirring at this temperature the deep colored solution is again cooled to −50° C. A solution of 11.6 g (49.8 mmol) of 1-benzyloxy-4-chloromethyl-benzene in 60 ml THF is dropped into the cooled solution. The system is allowed to heat to room temperature and stirred overnight. The solvent is evaporated and the residue that solidifies on cooling is stirred with ethyl ether and filtered. The residue is filtered through SiO2 eluting with dichloromethane. The yield is 3.75 g (20%).

後処理

  1. temperatureis again cooled to −50° C
  2. temperatureto heat to room temperature
  3. stirringstirred overnight
  4. customThe solvent is evaporated
  5. temperatureon cooling
  6. stirringis stirred with ethyl ether
  7. filtrationfiltered
  8. filtrationThe residue is filtered through SiO2 eluting with dichloromethane

出典と根拠

ORDレコード
ord-ca395e8fb5b7438997f54e1087e83bcd
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07557212B2

反応ノート

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