Tetrahydrofuran → HCID 4115493, compound

HRID 2417365Notes

Reaction equation

HRID 2417365 reaction equation
[I-].[CH:2]1([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:16]1COCC1>>[CH:2]1([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH2:16])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 12837Cyclohexyl phenyl ketoneHCID 30165Iodide Ion

Product 1

HCID 4115493HCID 4115493, compound

Conditions

Temperature
0 °C

Procedure

To a suspension of methylbiphenylphosphonium iodide in dry THF cooled at 0° C. was added NaNH2. After stirring for 15 h at ambient temperature, cyclohexylphenyl ketone Was added. The reaction mixture was stirred for 8 h at ambient temperature and then quenched with aqueous ammonium chloride and extracted with ethyl acetate. The combined organic phases were washed (brine), dried (Na2SO4) and concentrated. Silica gel column chromatography of the crude product using petroleum ether:EtOAc (49:1) as eluent gave α-cyclohexylstyrene as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred for 8 h at ambient temperature
  2. customquenched with aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed (brine)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-25c94e98ef1d4caf83732f10246ce253
Source dataset
uspto-grants-2004_11
Patent number
US06825378B2

Reaction notes

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