Water → Methyl alpha-Methyl-9-nitro-9,10-dihydroanthracene-10-acetate

HRID 1166000ノート

反応式

HRID 1166000 の反応式
[N+:1]([C:4]1[C:5]2[C:10]([CH:11]=[C:12]3[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2)([O-:3])=[O:2].CN([S+](N(C)C)N(C)C)C.C[Si-](F)(F)(C)C.OP([O-])(O)=O.[K+].[OH2:40].[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1>C(#N)C.CCOCC>[CH3:41][CH:42]([CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N+:1]([O-:3])=[O:2])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2)[C:43]([O:44][CH3:45])=[O:40]

参加物

8

反応物 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 117679-NitroanthraceneHCID 516951Monobasic potassium phosphateHCID 9795567Tris(dimethylamino)sulfonium difluorotrimethylsilicate

生成物 1

HCID 13507922Methyl alpha-Methyl-9-nitro-9,10-dihydroanthracene-10-acetate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 0.757 g (3.39 mmol) of 9-nitroanthracene and 0.663 mL (3.56 mmol) of MTS in 20 mL of anhydrous THF was added 0.941 g (3.42 mmol) of TASF in 2 mL of anhydrous acetonitrile at -78° C. The mixture was stirred for 24 hr. at -78° C. Then, ten mL of saturated KH2PO4 and 20 mL of water were added, the mixture was warmed to room temperature, and the product was extracted into ether. The combined ether extract was washed with water, dried, and concentrated. The major product, 0.491 g (56%), was isolated by column chromatography on silica using 20° ether/hexane as the solvent. Addition of small amount of ether to the major fraction yielded a light yellow solid. The product was analyzed by ultraviolet absorption, infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry.

後処理

  1. customat -78° C
  2. extractionthe product was extracted into ether
  3. extractionThe combined ether extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe major product, 0.491 g (56%), was isolated by column chromatography on silica using 20° ether/hexane as the solvent
  8. customyielded a light yellow solid
  9. customThe product was analyzed by ultraviolet absorption

出典と根拠

ORDレコード
ord-9182f7bc085e47f081c11faabea1d052
出典データセット
uspto-grants-1990_03
特許番号
US04912220

反応ノート

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