Diiodomethane → HCID 59527283, compound

HRID 384452Notes

Reaction equation

HRID 384452 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH2:2].[CH2:16]([Zn]CC)C.ICI.C([O-])(=O)C.[NH4+]>C(OCC)C>[CH:1]1([O:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:16][CH2:2]1

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 517165Ammonium AcetateHCID 59527293HCID 59527293, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 59527283HCID 59527283, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of {[4-(vinyloxy)butoxy]methyl}benzene (3.16 g) in diethyl ether (63 mL) was added diethyl zinc (1.0M, hexane solution) (30.6 mL) under nitrogen atmosphere, and a solution of diiodomethane (8.49 g) in diethyl ether (13 mL) was added dropwise thereto. The reaction liquid was stirred under reflux for 1 hour, followed by stirring at room temperature for 12 hours. A saturated aqueous ammonium acetate solution (80 mL) was added to the reaction liquid, followed by extraction with diethyl ether (400 mL). The organic layer was washed sequentially with a saturated aqueous ammonium acetate solution and saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=95/5) to obtain {[4-(cyclopropyloxy)butoxy]methyl}benzene (2.41 g).

Workup

  1. customThe reaction liquid
  2. temperatureunder reflux for 1 hour
  3. stirringby stirring at room temperature for 12 hours
  4. extractionfollowed by extraction with diethyl ether (400 mL)
  5. washThe organic layer was washed sequentially with a saturated aqueous ammonium acetate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-f8093346b7a5480f81a18884e7d38150
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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