Tetrahydrofuran → HCID 54189771, compound

HRID 129794Notes

Reaction equation

HRID 129794 reaction equation
[I-].[CH2:2]([Mg]Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:11]1[CH2:15][O:14][CH2:13][CH2:12]1>CCOCC.[NH4+].[Cl-].[Cu]I>[CH3:5][C:4]([CH2:3][CH2:8][CH2:7][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[CH:13][CH2:12][CH2:11][CH2:15][OH:14]

Participants

7

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 30165Iodide IonHCID 178418336HCID 178418336, compound

Product 1

HCID 54189771HCID 54189771, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.5 g (4.26 mmol) of the Example 35, Part B iodide in 10 mL of THF at 0° C. was added 12.9 mL (25.8 mmol) of benzylmagnesium chloride in THF (purchased from Aldrich Chemical) followed by 10 mg (catalyst) of copper (I) iodide. The reaction was stirred at 0° C. for 1 h, and at room temperature for 3 h. The reaction was diluted with ether and aqueous NH4Cl solution. The organic fraction was washed with water and brine, dried (MgSO4) and concentrated to provide 2.70 g of a crude oil. The oil was purified by flash chromatography (250 g of silica gel) eluting with 8:2 ethyl acetate/hexane to provide 1.10 g (99%) of title compound as a colorless oil.

Workup

  1. customat 0° C.
  2. waitat room temperature for 3 h
  3. washThe organic fraction was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto provide 2.70 g of a crude oil
  7. customThe oil was purified by flash chromatography (250 g of silica gel)
  8. washeluting with 8:2 ethyl acetate/hexane

Sources & evidence

ORD record
ord-0bc0b6af08454ae582996b6d3a8e0ef8
Source dataset
uspto-grants-1995_11
Patent number
US05470845

Reaction notes

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