2,2-Dimethoxypropane → HCID 66849068, compound

HRID 929456Notes

Reaction equation

HRID 929456 reaction equation
[CH3:1][O:2][C:3]([O:6][CH3:7])([CH3:5])[CH3:4].[I:8][C:9]1([CH2:12][C@@H](O)CO)[CH2:11][CH2:10]1>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[I:8][C:9]1([CH2:12][C@@H:1]2[CH2:7][O:6][C:3]([CH3:5])([CH3:4])[O:2]2)[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 66849286HCID 66849286, compound

Product 1

HCID 66849068HCID 66849068, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

2,2-Dimethoxypropane (140 mg, 1.337 mmol) and pyridinium p-toluenesulfonate (PPTS, 6 mg) were added to a solution of crude (R)-3-(1-iodocyclopropyl)propane-1,2-diol (step F, 0.598 mmol) dissolved in dichloromethane (3 mL) and the mixture stirred at room temperature for 2 hours. Solvents were removed under reduced pressure and the crude product purified by flash chromatography using ethyl acetate/hexane (1:10) eluant to afford (R)-4-((1-iodocyclopropyl)methyl)-2,2-dimethyl-1,3-dioxolane (84 mg, 50%).

Workup

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

Sources & evidence

ORD record
ord-4acd57746d6f492fb102575742cff8c4
Source dataset
uspto-grants-2016_03
Patent number
US09296686B2

Reaction notes

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