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

HRID 450960

Reaction equation

HRID 450960 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f38ad47adc164f30938f3185cfebd733
Source dataset
uspto-grants-2013_07
Patent number
US08487094B2

Linked notes

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