Water → HCID 10601564, 화합물

HRID 613638노트

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HRID 613638 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10831411HCID 10831411, 화합물HCID 18321849(2-Phthalimidoethyl)triphenylphosphonium bromide

생성물 2

HCID 10601564HCID 10601564, 화합물HCID 10625295HCID 10625295, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2c21b327badc4806830e45b255339640
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008229

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