Water → HCID 69997151、化合物

HRID 963430ノート

反応式

HRID 963430 の反応式
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4]1)[CH3:2].C([Si:22]([CH3:25])([CH3:24])[CH3:23])#C.O.[CH2:27](N(CC)CC)[CH3:28]>CN(C)C=O.[Cu]I>[CH2:27]([C:2]#[C:1][N:3]1[C:12]2[C:7](=[CH:8][C:9]([Si:22]([CH3:25])([CH3:24])[CH3:23])=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4]1)[CH3:28]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 619729HCID 619729、化合物

生成物 1

HCID 69997151HCID 69997151、化合物収率 80%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of ethyl 1-ethyl-6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate (Example 13h)), 1.94 ml of ethynyltrimethylsilane, 70 mg of bis-trimethylphosphine-palladium dichloride and 2.5 mg of copper(I) iodide in 7 ml of triethylamine and 7 ml of dimethylformamide is stirred at 60° for 9 hrs. After cooling to room temperature the reaction mixture is treated with 100 ml of water and extracted twice with 50 ml of methylene chloride each time. The combined organic phases are washed twice with 250 ml of water each time and once with 250 ml of a saturated, aqueous sodium chloride solution and dried over magnesium sulphate. The crude product is chromatographed on aluminium oxide (neutral, grade III) with n-hexane/ethyl acetate 1:1. 1.27 g (80%) of ethyl 1-ethyl-6-trimethylsilyl-ethynyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate are obtained.

後処理

  1. extractionextracted twice with 50 ml of methylene chloride each time
  2. washThe combined organic phases are washed twice with 250 ml of water each time
  3. dry with materialonce with 250 ml of a saturated, aqueous sodium chloride solution and dried over magnesium sulphate
  4. customThe crude product is chromatographed on aluminium oxide (neutral, grade III) with n-hexane/ethyl acetate 1:1

出典と根拠

ORDレコード
ord-b05545c695d14780a152db0bc7a6d2c2
出典データセット
uspto-grants-1998_06
特許番号
US05763450

反応ノート

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