Isopropanol → 1-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol

HRID 450960

반응식

HRID 450960 반응식
[CH:1]1[CH:6]=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3O)C2=C[CH:2]=1.CC(O)C.C([Sn](CC=C)(CC=C)CC=C)C=C.[Cl:40][CH2:41][CH2:42][C:43]([C:45]1[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=1)=[O:44]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(Cl)Cl>[Cl:40][CH2:41][CH2:42][C:43]([C:45]1[CH:46]=[CH:47][C:48]([F:51])=[CH:49][CH:50]=1)([OH:44])[CH2:6][CH:1]=[CH2:2]

참가 물질

7

반응물 4

HCID 3776IsopropanolHCID 11762BinolHCID 676722-Chloro-4'-fluoropropiophenoneHCID 81878Tetrallylstannane

생성물 1

HCID 534729381-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1,1′-bi-2-naphthol (0.2280 g, 0.80 mmol, 0.26 equiv), CH2Cl2 (5 mL) and titanium(IV) isopropoxide (0.2243 g, 0.79 mmol, 0.26 equiv) were added 2-propanol (3.1620 g, 52.6 mmol, 17 equiv), tetraallylstannane (1.2538 g, 4.43 mmol, 1.43 equiv), and 3-chloro-1-(4-fluorophenyl)propan-1-one (0.5760 g, 3.09 mmol, 1.0 equiv) successively. The reaction mixture was stirred at rt under nitrogen for 22 h. The reaction was quenched with satd aq NH4Cl and extracted with EtOAc. The organic layer was dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol as an oil.

후처리

  1. customThe reaction was quenched with satd aq NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customAfter the solvents were evaporated
  5. customthe residue was purified by chromatography on silica gel
  6. washeluted with hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-f38ad47adc164f30938f3185cfebd733
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487094B2

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