2,2-Dimethoxypropane → HCID 67086996, compound

HRID 1665097Notes

Reaction equation

HRID 1665097 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-1e907fbb9368451192cfc91650c064e8
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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