3-Chloropropiophenone → 1-Chloro-3-phenylhex-5-en-3-ol

HRID 406609노트

반응식

HRID 406609 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].[CH2:12]([Mg]Br)[CH:13]=[CH2:14]>C1COCC1>[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([OH:5])[CH2:14][CH:13]=[CH2:12]

참가 물질

4

반응물 2

HCID 702953-ChloropropiophenoneHCID 178455850HCID 178455850, 화합물

생성물 1

HCID 159334751-Chloro-3-phenylhex-5-en-3-ol수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 3-chloro-1-phenylpropan-1-one (170 g, 1.01 mol) in anhydrous THF (1200 mL) was added allylmagnesium bromide (1.2 L, 1 mol/L) at −78° C. under nitrogen. The formed mixture was stirred for 30 min at −78° C. The reaction was quenched with aqueous NaHCO3 solution. The organic phase was separated, dried over Na2SO4 and concentrated to give the crude product, which was purified by column chromatography (petroleum ether/EtOAc=100:1) to afford 1-chloro-3-phenylhex-5-en-3-ol (180 g, 86%). 1H NMR (CDCl3): 2.27 (m, 2H), 2.51 (m, 1H), 2.74 (m, 1H), 3.22 (m, 1H), 3.58 (m, 1H), 5.16 (m, 2H), 5.53 (m, 1H), 7.23 (m, 1H), 7.39 (m, 4H).

후처리

  1. customThe reaction was quenched with aqueous NaHCO3 solution
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by column chromatography (petroleum ether/EtOAc=100:1)

출처 및 근거

ORD 기록
ord-2654862977964e27b55ce369721df40c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754076B2

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