2,2-Dimethoxypropane → HCID 66916995, compound

HRID 882925Notes

Reaction equation

HRID 882925 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C@@H:11]([OH:14])[CH2:12][OH:13])=[CH:7][CH:6]=1.CO[C:19](OC)([CH3:21])[CH3:20].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CN(C=O)C>[CH3:20][C:19]1([CH3:21])[O:14][C@H:11]([CH2:10][O:9][C:8]2[CH:15]=[CH:16][C:5]([CH2:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=2)[CH2:12][O:13]1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 66917027HCID 66917027, compound

Product 1

HCID 66916995HCID 66916995, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-3-[4-(3-hydroxy-propyl)-phenoxy]-propane-1,2-diol (6.5 g, 28.7 mmol) in anhydrous DMF (100 mL) is added 2,2-dimethoxypropane (15.0 mL, 122.0 mmol) and pyridinium p-toluenesulfonate (0.75 g, 2.98 mmol). The reaction mixture is stirred at RT for 16 h and then concentrated in vacuo. The residue is dissolved in EtOAc and the organic portion is washed with 10% aqueous NaHCO3 solution, water, brine and dried over Na2SO4. The solvent is removed in vacuo and the crude product is purified by column chromatography (SiO2, EtOAc in petroleum ether, gradient 0-30% EtOAc) to obtain the title compound as a colourless oil. [M+H]+ 267.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc
  3. washthe organic portion is washed with 10% aqueous NaHCO3 solution, water, brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed in vacuo
  6. customthe crude product is purified by column chromatography (SiO2, EtOAc in petroleum ether, gradient 0-30% EtOAc)

Sources & evidence

ORD record
ord-c2844b9ef6704b079e1667149a788436
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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