tert-Butanol → HCID 86681378, 화합물

HRID 1406681노트

반응식

HRID 1406681 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 86681378HCID 86681378, 화합물수율 50%

시약·촉매·용매 2

HCID 24463Copper sulfate pentahydrate촉매HCID 962Water용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3535624e74574f99b1bf74c87900e8ad
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916705B2

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