Water → HCID 58950114、化合物

HRID 564309

反応式

HRID 564309 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[C:17]([F:18])=[C:16]([F:19])[CH:15]=[CH:14][C:13]=2[F:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:21]([O:26][CH3:27])(=[O:25])/[CH:22]=[CH:23]/[CH3:24].CC(C)([O-])C.[K+].O>C1COCC1.C(OCC)(=O)C>[CH3:27][O:26][C:21](=[O:25])[CH2:22][CH:23]([CH3:24])[CH:11]([S:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])[C:12]1[C:13]([F:20])=[CH:14][CH:15]=[C:16]([F:19])[C:17]=1[F:18]

参加物

7

反応物 4

HCID 962WaterHCID 638132Methyl CrotonateHCID 23665647Potassium tert-butoxideHCID 589503342-(4-Chloro-benzenesulfonylmethyl)-1,3,4-trifluoro-benzene

生成物 1

HCID 58950114HCID 58950114、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-(4-Chloro-phenylsulfanylmethyl)-1,3,4-trifluoro-benzene (Example 8, step 2, 1.0 g, 3.1 mmol) and methyl crotonate (1.55 g, 15.5 mmol) were dissolved in 50 mL of THF and potassium t-butoxide (1M in THF, 6.2 mL) was added. The reaction mixture was stirred at room temperature for five hours. 100 mL of water and 100 mL of EtOAc were added. The organic layer washed with brine (100 mL), dried over Na2SO4 and concentrated. The product was purified by column chromatography using EtOAc/hexane as the eluent (gradient from 0/100 to 50/50 in 40 min, 0.79 g, 60%). The product is a mixture of diastereomers. 1H NMR (CDCl3 400 MHz) δ 7.60 (m, 2H), 7.37 (m, 2H), 7.07 (m, 1H), 6.83 (m, 0.5H), 6.63 (m, 0.5H), 5.03 (t, J=10.2 Hz, 0.5H), 4.80 (d, J=10.2 Hz, 0.5H), 3.71 (s, 1.5H), 3.60 (s, 1.5H), 3.33 (m, 1H), 3.10 (m, 0.5H), 2.89 (m, 0.5H), 2.42 (m, 0.5H), 2.15 (m, 0.5H), 1.49 (t, J=6.6 Hz, 1.5H), 0.95 (dd, J=8.8 and 7.3 Hz, 1.5H).

後処理

  1. washThe organic layer washed with brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe product was purified by column chromatography
  5. customas the eluent (gradient from 0/100 to 50/50 in 40 min, 0.79 g, 60%)
  6. additiona mixture of diastereomers

出典と根拠

ORDレコード
ord-0ee7aea43a2e4dfab468dc0a18f321d4
出典データセット
uspto-grants-2011_11
特許番号
US08067621B2

関連ノート

読み込み中…