2,2-Dimethoxypropane → (S)-4-(2-iodoallyl)-2,2-dimethyl-1,3-dioxolane

HRID 929470Notes

Reaction equation

HRID 929470 reaction equation
[CH3:1][O:2][C:3]([O:6][CH3:7])([CH3:5])[CH3:4].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[I:25][C:26](=[CH2:32])[CH2:27][C@H](O)CO>ClCCl>[I:25][C:26](=[CH2:27])[CH2:32][C@H:1]1[CH2:7][O:6][C:3]([CH3:5])([CH3:4])[O:2]1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86667892(S)-4-iodopent-4-ene-1,2-diol

Product 1

HCID 86667891(S)-4-(2-iodoallyl)-2,2-dimethyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-Dimethoxypropane and pyridinium p-toluenesulfonate (PPTS) are added to a solution of (S)-4-iodopent-4-ene-1,2-diol in dichloromethane and the mixture stirred at room temperature for 2 hours. Solvents are removed under reduced pressure and the crude product purified by flash chromatography using ethyl acetate/hexane (1:10) eluant.

Workup

  1. customSolvents are removed under reduced pressure
  2. customthe crude product purified by flash chromatography

Sources & evidence

ORD record
ord-ed9a51352f9a43acb588499779ebf672
Source dataset
uspto-grants-2016_03
Patent number
US09296686B2

Reaction notes

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