2,2-Dimethoxypropane → HCID 67086996, compound

HRID 2365484Notes

Reaction equation

HRID 2365484 reaction equation
[CH3:1][O:2][C:3]([O:6][CH3:7])([CH3:5])[CH3:4].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[I:25][C:26]1[CH:37]=[CH:36][C:29]([O:30][CH2:31][C@@H](O)CO)=[CH:28][CH:27]=1>CN(C=O)C>[I:25][C:26]1[CH:37]=[CH:36][C:29]([O:30][CH2:31][C@@H:1]2[CH2:7][O:6][C:3]([CH3:5])([CH3:4])[O:2]2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67086796HCID 67086796, compound

Product 1

HCID 67086996HCID 67086996, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,2-Dimethoxypropane (1.94 ml, 15.8 mmol) and PPTS (0.079 mg, 0.32 mmol) are added to a solution of (S)-3-(4-Iodo-phenoxy)-propane-1,2-diol (0.93 g, 3.16 mmol) in DMF (20 ml), and the resulting solution is left to stir at room temperature overnight. The solvent is removed in vacuo and the residue is purified by chromatography (SiO2, EtOAc:Iso-hexane) to afford (R)-4-(4-Iodo-phenoxymethyl)-2,2-dimethyl-[1,3]dioxolane as a colourless oil.

Workup

  1. waitthe resulting solution is left
  2. customThe solvent is removed in vacuo
  3. customthe residue is purified by chromatography (SiO2, EtOAc:Iso-hexane)

Sources & evidence

ORD record
ord-cabd836253be432596a9b7ba92c953fc
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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