2-Chloro-4'-fluoropropiophenone → 1-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol

HRID 403573

반응식

HRID 403573 반응식
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[Cl:6][CH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:10]>C1COCC1>[Cl:6][CH2:7][CH2:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)([OH:10])[CH2:3][CH:2]=[CH2:1]

참가 물질

4

반응물 2

HCID 676722-Chloro-4'-fluoropropiophenoneHCID 178455850HCID 178455850, 화합물

생성물 1

HCID 534729381-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A 1000-mL flask was charged with anhydrous CeCl3 (50 g, 0.2 mol) and THF (360 mL). The mixture was vigorously stirred for 3.5 h at rt. The suspension was then cooled to −78° C., and a solution of allylmagnesium bromide (1.0 M in THF, 188.2 mL, 188 mmol) was added. After stirring for 2 h at −78° C., a solution of 3-chloro-1-(4-fluorophenyl)propan-1-one (22.6 g, 120 mmol) in THF (269 mL) was added dropwise. The reaction mixture was allowed to slowly warm to rt while stirring overnight. The reaction was then quenched with satd aq NaHCO3, extracted with EtOAc and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford of 1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (23.8 g, 87%) as an oil. 1H NMR (CDCl3): 2.27 (m, 1H), 2.31 (m, 2H), 2.50 (m, 1H), 2.69 (m, 1H), 3.19 (m, 1H), 3.52 (m, 1H), 5.16 (m, 2H), 5.51 (m, 1H), 7.04 (m, 2H), 7.35 (m, 2H).

후처리

  1. temperatureThe suspension was then cooled to −78° C.
  2. stirringAfter stirring for 2 h at −78° C.
  3. temperatureto slowly warm to rt
  4. stirringwhile stirring overnight
  5. customThe reaction was then quenched with satd aq NaHCO3
  6. extractionextracted with EtOAc
  7. dry with materialdried over Na2SO4
  8. customAfter the solvents were evaporated
  9. customthe residue was purified by chromatography on silica gel
  10. washeluted with hexanes/EtOAc

출처 및 근거

ORD 기록
ord-cb15371dfa654a89998894a701dda42d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748444B2

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