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

HRID 406611노트

반응식

HRID 406611 반응식
[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]

참가 물질

6

반응물 3

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 702953-Chloropropiophenone

생성물 1

HCID 159334751-Chloro-3-phenylhex-5-en-3-ol수율 97.3%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1f56cfcc616c42c587a445714b3e956d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754076B2

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