Water → HCID 58097238, compound

HRID 1500109Notes

Reaction equation

HRID 1500109 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.ClC[C@@H:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:18][C:15]1([CH3:19])[O:16][C@H:17]([CH2:1][O:2][C:3]2[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=2)[CH2:13][O:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 312444-MethoxybenzaldehydeHCID 6930483(S)-4-Chloromethyl-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 58097238HCID 58097238, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g (16.38 mmol) of p-methoxybenzaldehyde together with 3.7 g (24.57 mmol) of (4S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane and 15.8 g (114.64 mmol) of potassium carbonate are stirred in 10 ml of DMF at 130° C. overnight. The mixture is then added to water and extracted with methylene chloride. The organic phase is washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated. The residue is purified on a silica gel column (mobile phase: cyclohexane/ethyl acetate 5:1). This gives 2.42 g (61% of theory) of the target compound.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phase is washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customThe residue is purified on a silica gel column (mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-4c2f643a062a4c88b766f04cae0bb3ed
Source dataset
uspto-grants-2015_12
Patent number
US09205077B2

Reaction notes

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