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

HRID 2037429

反応式

HRID 2037429 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 6344Dichloromethane溶媒

実験手順

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/EtOAc to afford 1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol as an oil.

後処理

  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/EtOAc

出典と根拠

ORDレコード
ord-68f53296634847b78f8625e71ce4641c
出典データセット
uspto-grants-2013_11
特許番号
US08575156B2

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