Diiodomethane → 1-[2-(Cyclopropylmethoxy)ethyl]-4-(phenylmethoxy)benzene

HRID 1745867Notes

Reaction equation

HRID 1745867 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH:2]=[CH2:3].I[CH2:22]I>CCOCC>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][O:4][CH2:1][CH:2]2[CH2:22][CH2:3]2)=[CH:8][CH:9]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6346DiiodomethaneHCID 22227278HCID 22227278, compound

Product 1

HCID 115146971-[2-(Cyclopropylmethoxy)ethyl]-4-(phenylmethoxy)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of Zn/Cu couple (3.24 g) and dry ether (20 ml) was added to the compound of formula (7), (2 g, 0.0075 mol) in ether (10 ml) followed by the addition of diiodomethane (4.2 ml, 0.052 mol). The reaction mixture was refluxed under nitrogen atmosphere for 72 h (monitored by TLC) and filtered. The filtrate was washed with water, dried, concentrated and the residue purified by column chromatography on silica gel, eluting with light petroleum ether:ethyl acetate(2:50) to afford pure product of formula (8), as an oil 1.8 g (85%).

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen atmosphere for 72 h (monitored by TLC)
  2. filtrationfiltered
  3. washThe filtrate was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue purified by column chromatography on silica gel
  7. washeluting with light petroleum ether:ethyl acetate(2:50)

Sources & evidence

ORD record
ord-44b25bb211304a6981e5249bc99ac7bc
Source dataset
uspto-grants-2006_03
Patent number
US07019172B2

Reaction notes

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