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Hydrochloric Acid → 4-[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzylidene]tetrahydropyran

HRID 1766657
ノート
印刷プレビュー

反応式

HRID 1766657 の反応式
[Cl-].[CH2:2]([O:9][C:10]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[C:45]([CH3:46])=[CH:44][C:43]([N+:47]([O-:49])=[O:48])=[C:42]3[C:38]=2[CH2:39][CH2:40][CH2:41]3)=[CH:32][C:11]=1[CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[O:52]1[CH2:57][CH2:56][C:55](=O)[CH2:54][CH2:53]1.Cl>CS(C)=O>[CH2:2]([O:9][C:10]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[C:45]([CH3:46])=[CH:44][C:43]([N+:47]([O-:49])=[O:48])=[C:42]3[C:38]=2[CH2:39][CH2:40][CH2:41]3)=[CH:32][C:11]=1[CH:12]=[C:55]1[CH2:56][CH2:57][O:52][CH2:53][CH2:54]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 21110566[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzyl]triphenylphosphonium chloride

生成物 1

HCID 211105754-[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzylidene]tetrahydropyran

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒

実験手順

To a suspension of [2-benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzyl]triphenylphosphonium chloride (559 mg) in dimethylsulfoxide (20 mL) was added sodium hydride (60%, 49 mg) at room temperature, the mixture was stirred for 15 min. After adding tetrahydro-4H-pyran-4-one (0.15 mL), the reaction mixture was stirred at room temperature for 6 hours. After adding dropwise diluted hydrochloric acid to make the mixture acidify fully, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed-under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate) to give the title compound (230 mg).

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 6 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-6043ef445ded4f7badcd4be2cb900cc0
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07230031B2

反応ノート

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