2,2-Dimethoxypropane → HCID 66916995, compound

HRID 1665138Notes

Reaction equation

HRID 1665138 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 mmol) and 2,2-dimethoxypropane (31 ml, 250 mmol). The mixture is stirred at room temperature for 18 hours 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 chromatography on silica eluting with 1:4 EtOAc/iso-hexane to 1:1 EtOAc/iso-hexane to afford (3-[4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-propan-1-ol as a colourless oil; 1H NMR (CDCl3): 1.25 (1H, br), 1.39 (3H, s), 1.43 (3H, s), 1.85 (2H, pent, J=6.9 Hz), 2.63 (2H, tr, J=6.9 Hz), 3.63 (2H, tr, J=6.9 Hz), 3.90 (2H, m), 4.02 (1H, m), 4.12 (1H, m), 4.50 (1H, pent, J=6.8 Hz), 6.82 (2H, d, J=7.4 Hz), 7.10 (2H, d, J=7.4 Hz).

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 chromatography on silica eluting with 1:4 EtOAc/iso-hexane to 1:1 EtOAc/iso-hexane

Sources & evidence

ORD record
ord-1ec4d8d33c814bcf8805687b1c4ce4a8
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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