Potassium Carbonate → 6-Ethynylisoquinoline

HRID 598840ノート

反応式

HRID 598840 の反応式
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[N:10][CH:9]=[CH:8]2.C(=O)([O-])[O-].[K+].[K+]>CO.CCOC(C)=O.O>[C:4]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[N:10][CH:9]=[CH:8]2)#[CH:3]

参加物

6

反応物 2

HCID 11430Potassium CarbonateHCID 579505646-((Trimethylsilyl)ethynyl)isoquinoline

生成物 1

HCID 579505416-Ethynylisoquinoline収率 87%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-(2-(trimethylsilyl)ethynyl)isoquinoline (2.2 g, 9.8 mmol) in 45 mL of MeOH was added potassium carbonate (2.7 g, 20 mmol). After 1 hour, the reaction mixture was diluted with 100 mL of EtOAc and 50 mL of water. The mixture was partitioned and the aqueous portion was extracted three times with 50 mL of EtOAc. The combined organic layers were washed with 100 mL of brine and dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (5% to 30% EtOAc/hexanes) afforded 6-ethynylisoquinoline (1.3 g, 87% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ pp 9.25 (s, 1H), 8.56 (d, J=5.7 Hz, 1H), 7.99 (s, 1H), 7.93 (d, J=8.4 Hz, 1H), 7.65 (dd, J=1.2 Hz, 8.6 Hz, 1H), 7.62 (d, J=5.8 Hz, 1H), 3.26 (s, 1H).

後処理

  1. customThe mixture was partitioned
  2. extractionthe aqueous portion was extracted three times with 50 mL of EtOAc
  3. washThe combined organic layers were washed with 100 mL of brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration under reduced pressure

出典と根拠

ORDレコード
ord-8e18e16dd8e347b98fd2138a50f09876
出典データセット
uspto-grants-2011_03
特許番号
US07897619B2

反応ノート

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