2,2-Dimethoxypropane → HCID 57682793, compound

HRID 494982Notes

Reaction equation

HRID 494982 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([CH2:19][CH:20]([OH:23])[CH2:21][OH:22])=[C:12]([O:24][CH3:25])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO[C:28](OC)([CH3:30])[CH3:29].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O>[C:4]([Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([O:24][CH3:25])[C:13]([CH2:19][CH:20]2[CH2:21][O:22][C:28]([CH3:30])([CH3:29])[O:23]2)=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])([CH3:2])[CH3:3])([CH3:5])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57682845HCID 57682845, compound

Product 1

HCID 57682793HCID 57682793, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

390 mg of 3-(4-(t-butyldimethylsilyloxy-methyl)-2-methoxy-5-nitrophenyl)propane-1,2-diol was dissolved in 8 ml of acetone. Then, 0.33 g of dimethoxypropane and 26 mg of pyridinium p-toluenesulfonate were added to the reaction solution. The obtained mixture was then stirred at room temperature for 41 hours. Thereafter, the reaction solution was concentrated under a reduced pressure. The residue was diluted with ethyl acetate and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 358 mg of the subject compound.

Workup

  1. concentrationThereafter, the reaction solution was concentrated under a reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c85d5f185899443d9da23764f49342a0
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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