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

HRID 588909ノート

反応式

HRID 588909 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 904560122-Chloro-4-methoxy-1-vinylbenzene収率 53.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f1fb33f26ac640f8b27e9dcf042cac18
出典データセット
uspto-grants-2016_01
特許番号
US09227978B2

反応ノート

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