2,2-Dimethoxypropane → HCID 56968061, compound

HRID 1028881Notes

Reaction equation

HRID 1028881 reaction equation
[N+:1]([C:4]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH2:7][OH:8])[CH2:5][OH:6])([O-:3])=[O:2].CO[C:19](OC)([CH3:21])[CH3:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.C(OCC)(=O)C>[CH3:20][C:19]1([CH3:21])[O:8][CH2:7][C:4]([N+:1]([O-:3])=[O:2])([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:5][O:6]1

Participants

6

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 66837691HCID 66837691, compound

Product 1

HCID 56968061HCID 56968061, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-nitro-2-phenethylpropane-1,3-diol (19) (40.0 mmol) in DMF (40 ml) was added 2,2-dimethoxypropane (6.0 ml, 50 mmol) and p-toluenesulfonic acid monohydrate (400 mg, 2.0 mmol) and stirring was continued overnight. The reaction mixture was diluted with ethyl acetate, washed with saturated NaHCO3 and brine, dried, and concentrated. The residue was pure enough for transformation to the next step or could be purified by silica gel column chromatography.

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated
  4. customcould be purified by silica gel column chromatography

Sources & evidence

ORD record
ord-08aaf83b03ef4b7a96705592a8b64d78
Source dataset
uspto-grants-2014_05
Patent number
US08735627B2

Reaction notes

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