Glyceryl Allyl Ether → 4-((allyloxy)methyl)-N,N-dimethyl-1,3,2-dioxarsolan-2-amine

HRID 534662

Reaction equation

HRID 534662 reaction equation
[CH3:1][N:2]([As:4](N(C)C)N(C)C)[CH3:3].[CH2:11]([O:14][CH2:15][CH:16]([OH:19])[CH2:17][OH:18])[CH:12]=[CH2:13]>CCCCCC>[CH2:11]([O:14][CH2:15][CH:16]1[CH2:17][O:18][As:4]([N:2]([CH3:3])[CH3:1])[O:19]1)[CH:12]=[CH2:13]

Participants

4

Reactant 2

HCID 78950Glyceryl Allyl EtherHCID 165514N-[bis(dimethylamino)arsanyl]-N-methylmethanamine

Product 1

HCID 867176874-((allyloxy)methyl)-N,N-dimethyl-1,3,2-dioxarsolan-2-amine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

is formed when at room temperature, about 0.5 g (0.445 mL, 2.414 mmol, 1.1 equivalents) of tris(dimethylamino)arsine (TDMA), is added to about 10 mL dry hexane in a 25 mL round-bottom flask, and then about 0.29 g (0.27 mL, 2.19 mmol, 1.0 equivalents) of 3-(allyloxy)propane-1,2-diol is added dropwise into the system. The mixture is heated to reflux under nitrogen for about one hour, and then cooled to room temperature. Removal of the solvent in vacuum gives crude 4-((allyloxy)methyl)-N,N-dimethyl-1,3,2-dioxarsolan-2-amine as an oil.

Workup

  1. customis formed when at room temperature
  2. temperatureThe mixture is heated
  3. temperatureto reflux under nitrogen for about one hour
  4. customRemoval of the solvent in vacuum

Sources & evidence

ORD record
ord-d965bae987d640fdb842bd4418f8dac3
Source dataset
uspto-grants-2014_10
Patent number
US08853438B2

Linked notes

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