Allyl bromide → 1-Chloro-3-phenylhex-5-en-3-ol

HRID 333890

反応式

HRID 333890 の反応式
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[NH4+].[Cl-].[CH2:14](Br)[CH:15]=[CH2:16]>C1COCC1.[Zn]>[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([OH:5])[CH2:16][CH:15]=[CH2:14]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 702953-Chloropropiophenone

生成物 1

HCID 159334751-Chloro-3-phenylhex-5-en-3-ol収率 97.3%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 3-chloro-1-phenylpropan-1-one (100 g, 0.595 mol) in THF (280 ml) was added dropwise to a well-stirred mixture of zinc powder (need not be activated) (40 g, 1.231 mol, satd aq NH4Cl solution (1500 ml) and THF (400 ml). Allyl bromide (143 g, 1.19 mol) was dissolved in THF (200 ml) was slowly added to the reaction mixture. The reaction was mildly exothermic, and the mixture began to reflux spontaneously. After refluxing had ceased, the mixture was stirred for 1 h. The mixture was extracted with EtOAc, dried over anhydrous Na2SO4, and concentrated to give 1-chloro-3-phenylhex-5-en-3-ol (122 g, 97%). 1H NMR: (400 MHz, CDCl3): δ=2.24 (s, 1H), 2.34 (m, 2H), 2.53 (m, 1H), 2.75 (m, 1H), 3.20 (m, 1H), 3.58 (m, 1H), 5.18 (t, 1H), 5.51 (m, 1H), 7.26 (m, 1H), 7.26-7.39 (m, 3H).

後処理

  1. additionwas slowly added to the reaction mixture
  2. temperatureto reflux spontaneously
  3. temperatureAfter refluxing
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-62322239fe214a53b55df36564a28d4a
出典データセット
uspto-grants-2014_11
特許番号
US08883778B2

関連ノート

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