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

HRID 564311

반응식

HRID 564311 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-9f774f98be4b49f382f3174b0d099a64
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067621B2

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