Water → HCID 10601564、化合物

HRID 1699205ノート

反応式

HRID 1699205 の反応式
[H-].[Na+].[Br-].[C:4]1(=[O:35])[N:8]([CH2:9][CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:7](=[O:30])[C:6]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:5]12.[Cl:36][C:37]1[C:55]([CH:56]=O)=[CH:54][CH:53]=[C:52]([Cl:58])[C:38]=1[CH2:39][O:40][C:41]1[CH:42]=[CH:43][CH:44]=[C:45]2[C:50]=1[N:49]=[C:48]([CH3:51])[CH:47]=[CH:46]2.O>CS(C)=O>[Cl:36][C:37]1[C:55](/[CH:56]=[CH:10]\[CH2:9][N:8]2[C:4](=[O:35])[C:5]3=[CH:34][CH:33]=[CH:32][CH:31]=[C:6]3[C:7]2=[O:30])=[CH:54][CH:53]=[C:52]([Cl:58])[C:38]=1[CH2:39][O:40][C:41]1[CH:42]=[CH:43][CH:44]=[C:45]2[C:50]=1[N:49]=[C:48]([CH3:51])[CH:47]=[CH:46]2.[Cl:36][C:37]1[C:55](/[CH:56]=[CH:10]/[CH2:9][N:8]2[C:4](=[O:35])[C:5]3=[CH:34][CH:33]=[CH:32][CH:31]=[C:6]3[C:7]2=[O:30])=[CH:54][CH:53]=[C:52]([Cl:58])[C:38]=1[CH2:39][O:40][C:41]1[CH:42]=[CH:43][CH:44]=[C:45]2[C:50]=1[N:49]=[C:48]([CH3:51])[CH:47]=[CH:46]2

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10831411HCID 10831411、化合物HCID 18321849(2-Phthalimidoethyl)triphenylphosphonium bromide

生成物 2

HCID 10601564HCID 10601564、化合物HCID 10625295HCID 10625295、化合物

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

The mixture of 60% sodium hydride in oil (56 mg) and dimethyl sulfoxide (6 ml) was stirred at 60° C. under nitrogen atmosphere for 1 hour. To the mixture was added (2-phthalimidoethyl)triphenylphosphonium bromide (1.19 g) at ambient temperature, and the mixture was stirred for 30 minutes. To the mixture was added 8-(2,6-dichloro-3-formylbenzyloxy)-2-methylquinoline (400 mg) under water bath cooling, and the mixture was stirred overnight. To the reaction mixture was added water and extracted with chloroform. The organic layer was washed with water three times and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash silica gel chromatography eluted with n-hexane-ethyl acetate to give 8-[2,6-dichloro-3-((Z)-3-phthalimido-1-propenyl)benzyloxy]-2-methylquinoline as amorphous first and 8-[2,6-dichloro-3-((E)-3-phthalimido-1-propenyl)benzyloxy]-2-methylquinoline as amorphous second. The former was crystallized from diisopropyl ether to afford pale yellow crystals (138 mg). The latter was crystallized from diisopropyl ether to afford pale yellow crystals (192 mg).

後処理

  1. stirringthe mixture was stirred for 30 minutes
  2. temperaturecooling
  3. stirringthe mixture was stirred overnight
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with water three times and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by flash silica gel chromatography
  9. washeluted with n-hexane-ethyl acetate

出典と根拠

ORDレコード
ord-50408b04f18a46d18701464bdd61182c
出典データセット
uspto-grants-2002_02
特許番号
US06344462B1

反応ノート

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