2,2-Dimethoxypropane → HCID 66916995, compound

HRID 1183033Notes

Reaction equation

HRID 1183033 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.[C:17]1(C)[CH:22]=CC(S([O-])(=O)=O)=C[CH:18]=1.[NH+]1C=CC=CC=1.COC(OC)(C)C>CN(C=O)C>[CH3:18][C:17]1([CH3:22])[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 (S)-3-[4-(3-hydroxy-propyl)-phenoxy]-propane-1,2-diol (11.5 g, 50.9 mmol) in dry DMF (150 mL) is added pyridinium p-toluenesulfonate (1.28 g, 5.0 mmol) and 2,2-dimethoxypropane (31 mL, 250 mmol). The mixture is stirred at RT for 18 h and then the solvent is removed in vacuo. The residue is dissolved in EtOAc (150 mL) and washed with water, saturated aqueous sodium hydrogen carbonate solution, brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, EtOAc:iso-hexane, gradient 20% to 50% EtOAc) to afford the title compound as a colourless oil.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in EtOAc (150 mL)
  3. washwashed with water, saturated aqueous sodium hydrogen carbonate solution, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (SiO2, EtOAc:iso-hexane, gradient 20% to 50% EtOAc)

Sources & evidence

ORD record
ord-12c75bff596543f5b4f6f55513d816ab
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

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