tert-Butanol → HCID 86681378、化合物

HRID 1406681ノート

反応式

HRID 1406681 の反応式
[C:1]([C:3]1[CH:10]=[C:7]([CH:8]=[O:9])[C:6]([OH:11])=[CH:5][CH:4]=1)#[CH:2].[CH2:12]([N:19]=[N+:20]=[N-:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(O)(C)C.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:12]([N:19]1[CH:2]=[C:1]([C:3]2[CH:4]=[CH:5][C:6]([OH:11])=[C:7]([CH:10]=2)[CH:8]=[O:9])[N:21]=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 450835745-Ethynyl-2-hydroxybenzaldehyde

生成物 1

HCID 86681378HCID 86681378、化合物収率 50%

試薬・触媒・溶媒 2

HCID 24463Copper sulfate pentahydrate触媒HCID 962Water溶媒2 回

実験手順

5-ethynylsalicylaldehyde (2{26}, 50 mg, 0.34 mmol, 1.0 equiv.) and benzyl azide (91 mg, 86 μL, 0.68 mmol, 2.0 equiv.) were suspended in 1:1 t-BuOH:H2O (1.2 mL). Sodium L-ascorbate (24 mg in 100 μL H2O, 0.34 mmol, 1.0 equiv.) was added, followed by copper (II) sulfate pentahydrate (67 mg in 200 μL H2O, 0.10 mmol, 0.33 equiv.). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with H2O (10 mL), and the aqueous layer was extracted with DCM (3×10 mL). The combined organic layers were washed with brine (10 mL), dried over Mg504, filtered, and concentrated. The crude product was purified by silica gel column chromatography (25-50% EtOAc/hexanes) to yield 2{27} (47.5 mg, 0.17 mmol, 50.0%) as an off-white solid. 1H-NMR (500 MHz, CDCl3): δ 11.03 (s, 1H), 9.92 (s, 1H), 8.07 (d, 1H, J=2.5 Hz), 7.86 (dd, 1H, J=2.0, 8.0 Hz), 7.65 (s, 1H), 7.41-7.35 (m, 3H), 7.31 (dd, 2H, J=2.0, 7.5 Hz), 7.01 (d, 1H, J=8.5 Hz), 5.57 (s, 2H). 13C-NMR (125 MHz, CDCl3): δ 196.5, 161.3, 134.4, 134.2, 130.6, 129.1, 128.8, 128.1, 124.9, 122.9, 120.6, 118.9, 118.1, 54.3.

後処理

  1. extractionthe aqueous layer was extracted with DCM (3×10 mL)
  2. washThe combined organic layers were washed with brine (10 mL)
  3. customdried over Mg504
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (25-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-3535624e74574f99b1bf74c87900e8ad
出典データセット
uspto-grants-2014_12
特許番号
US08916705B2

反応ノート

読み込み中…