Phosphonium → 2-Chloro-4-methoxy-1-vinylbenzene

HRID 588909노트

반응식

HRID 588909 반응식
[PH4+].[CH3:2]C([O-])(C)C.[K+].[Cl:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:10]=1[CH:11]=O>C1COCC1.C([O-])(O)=O.[Na+]>[Cl:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:10]=1[CH:11]=[CH2:2]

참가 물질

6

반응물 3

HCID 5460504PhosphoniumHCID 93617462-Chloro-4-methoxybenzaldehydeHCID 23665647Potassium tert-butoxide

생성물 1

HCID 904560122-Chloro-4-methoxy-1-vinylbenzene수율 53.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a suspension of phosphonium salt (2.05 g, 5 mmol) in THF (50 mL), was added t-BuOK (0.84 g, 7.5 mmol). The mixture turned to yellow and was kept stirring at RT for 1 h. 2-Chloro-4-methoxybenzaldehyde (0.85 g, 5 mmol) was added to the mixture. The mixture was stirred for 24 h, diluted with sat. NaHCO3 and then extracted with hexane. Organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Isolera One (100% hexanes to afford the desired product (0.45 g, 53% yield). 1H NMR (CDCl3, δ): 7.49 (d, J=6.8 Hz, 1H), 7.03 (dd, J=8.8, 14.0 Hz, 1H), 6.90 (d, J=2.0, 1H), 6.79 (dd, J=2.0, 6.8 Hz, 1H), 5.62 (d, J=14.0 Hz, 1H), 5.26 (d, J=8.8 Hz, 1H), 3.80 (s, 3H).

후처리

  1. stirringThe mixture was stirred for 24 h
  2. extractionextracted with hexane
  3. dry with materialOrganic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Isolera One (100% hexanes

출처 및 근거

ORD 기록
ord-f1fb33f26ac640f8b27e9dcf042cac18
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227978B2

반응 노트

불러오는 중…