Methanol, 1,1-diethoxy-, 1-acetate → HCID 178455035, compound

HRID 1351997Notes

Reaction equation

HRID 1351997 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[C:10]=1[NH2:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:17](OC(OCC)OCC)(=O)C>>[Si:1]([O:8][C:9]1[C:10]2[NH:16][CH:17]=[N:15][C:11]=2[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 223857163-[(Tert-butyldimethylsilyl)oxy]benzene-1,2-diamine

Product 1

HCID 178455035HCID 178455035, compoundYield 43%

Procedure

To 3-{[tert-butyl(dimethyl)silyl]oxy}benzene-1,2-diamine (4.27 g, 17.9 mmol) is added diethoxymethyl acetate (8.7 g, 53.6 mmol), and the mixture is stirred at room temperature for 5 hours. The precipitated white solid is collected by filtration, and the filtrate is further stirred at room temperature for 12 hours. The precipitated white solid is collected by filtration, and washed with a small amount of hexane. The filtrate is concentrated under reduced pressure, ant the obtained residue is purified by silica gel column chromatography (ammonic chloroform) to give the title compound as white solid (1.89 g, yield: 43%).

Workup

  1. filtrationThe precipitated white solid is collected by filtration
  2. stirringthe filtrate is further stirred at room temperature for 12 hours
  3. filtrationThe precipitated white solid is collected by filtration
  4. washwashed with a small amount of hexane
  5. concentrationThe filtrate is concentrated under reduced pressure, ant the obtained residue
  6. customis purified by silica gel column chromatography (ammonic chloroform)

Sources & evidence

ORD record
ord-2b5c115065ab412c8286ccfe2f5cdcf7
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

Loading…