Water → 7-(4-Chloro-benzenesulfonyl)-7-(2,3,6-trifluoro-phenyl)-1-heptene

HRID 564311

反応式

HRID 564311 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.Br[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27].CC(C)([O-])C.[K+].O>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:12]2[C:13]([F:20])=[CH:14][CH:15]=[C:16]([F:19])[C:17]=2[F:18])[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]=[CH2:22])(=[O:10])=[O:9])=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 759066-Bromo-1-hexeneHCID 23665647Potassium tert-butoxideHCID 589503342-(4-Chloro-benzenesulfonylmethyl)-1,3,4-trifluoro-benzene

生成物 1

HCID 589500547-(4-Chloro-benzenesulfonyl)-7-(2,3,6-trifluoro-phenyl)-1-heptene

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-(4-Chloro-benzenesulfonylmethyl)-1,3,4-trifluoro-benzene (1.0 g, 3.1 mmol, from example 8, step 2) and 6-bromo-1-hexene (1.5 g, 6.3 mmole) were dissolved in 20 mL THF and potassium t-butoxide (1M in THF, 6.2 mL) was added. The reaction mixture was stirred at room temperature for three hours. 50 mL water and 50 mL EtOAc were added. The organic layer washed with brine (50 mL), dried over Na2SO4 and concentrated. The product was purified by column chromatography using EtOAc/Hexane as eluent (gradient from 0/100 to 25/75 in 40 minutes, 0.65 g, 52%). 1H NMR (CDCl3, 400 MHz) δ 7.63 (d, j=8.05 Hz, 2H), 7.45 (d, j=8.05 Hz, 2H), 7.14 (m, 1H), 6.83 (m, 0.5H), 6.74 (m, 0.5H), 5.70 (m, 1H), 4.93 (m, 2H), 4.58 (d, j=5.1 and 6.5 Hz, 1H), 2.43 (m, 1H), 2.31 (m, 1H), 1.99 (m, 2H), 1.39 (m, 2H), 1.25 (m, 2H).

後処理

  1. washThe organic layer washed with brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe product was purified by column chromatography
  5. custom(gradient from 0/100 to 25/75 in 40 minutes, 0.65 g, 52%)

出典と根拠

ORDレコード
ord-9f774f98be4b49f382f3174b0d099a64
出典データセット
uspto-grants-2011_11
特許番号
US08067621B2

関連ノート

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