Diiodomethane → HCID 54311717, compound

HRID 729117Notes

Reaction equation

HRID 729117 reaction equation
[CH2:1]([Zn]CC)C.[CH:6]([O:8][CH2:9][CH2:10][CH2:11][C:12]([CH3:35])=[CH:13][CH2:14][CH2:15][C:16]([CH3:34])=[CH:17][CH2:18][CH2:19][CH:20]=[C:21]([CH3:33])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:32])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])=[CH2:7].ICI>CCOCC>[CH:6]1([O:8][CH2:9][CH2:10][CH2:11][C:12]([CH3:35])=[CH:13][CH2:14][CH2:15][C:16]([CH3:34])=[CH:17][CH2:18][CH2:19][CH:20]=[C:21]([CH3:33])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:32])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[CH2:1][CH2:7]1

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 57174086HCID 57174086, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 54311717HCID 54311717, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Diethyl zinc (0.606 ml, 1.0 M in hexane) was added to 4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaen-1-ol vinyl ether (0.250 g, 0.606 mmol) in 6 ml ether under argon. Diiodomethane (0.240 g, 0.606 mmol, 73.3 μl), in 2 ml ether, was added dropwise over 0.5 hour. After stirring overnight at room temperature, the reaction was quenched with saturated ammonium chloride. An additional 40 ml of ether and 20 ml of saturated ammonium chloride were added and the layers separated. The ether layer was washed with brine and dried over magnesium sulfate. Removal of the solvent in vacuo yielded 0.32 g of crude product, which wasshown to be a 3:1 mixture by capillary gas chromatography of 4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentane-1-ol cyclopropyl etherand a dicyclopropyl compound.

Workup

  1. customthe reaction was quenched with saturated ammonium chloride
  2. additionAn additional 40 ml of ether and 20 ml of saturated ammonium chloride were added
  3. customthe layers separated
  4. washThe ether layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-64138a880cac49a2bbb8bc1ec728585d
Source dataset
uspto-grants-1991_09
Patent number
US05051534

Reaction notes

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