Potassium Carbonate → HCID 118597856、化合物

HRID 63624

反応式

HRID 63624 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[SH:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[S:18][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:12])[CH2:7][CH2:8][O:9][C:10]=2[CH:11]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 5226742-ThiophenethiolHCID 223357367-Bromo-2,3-dihydro-4H-1-benzopyran-4-one

生成物 1

HCID 118597856HCID 118597856、化合物収率 93%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
78 °C

実験手順

7-Bromochroman-4-one (1.5 g, 6.6 mmol), thiophene-2-thiol (0.68 mL, 7.3 mmol), and potassium carbonate (1.37 g, 9.9 mmol) were combined in ACN (50 mL) in a sealed vessel, and the reaction was heated at 78° C. overnight. The reaction was cooled, filtered, and concentrated. Purification by silica gel chromatography (10-60% EtOAc/hexanes) gave 1.6 g (93%) of the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 2.75 (2H, t, J=6.4 Hz), 4.48 (2H, t, J=6.4 Hz), 6.59 (1H, d, J=1.8 Hz), 6.75 (1H, dd, J=8.4, 1.8 Hz), 7.13-7.17 (1H, m), 7.34 (1H, dd, J=3.6, 1.2 Hz), 8.58 (1H, dd, J=5.4, 1.2 Hz), 7.75 (1H, d, J=8.4 Hz). [M+H] calc'd for C13H10O2S2, 263. found 263.

後処理

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (10-60% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-40636259d92e4e79a5ce18e7e2203aa7
出典データセット
uspto-grants-2016_09
特許番号
US09447046B2

関連ノート

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