p-Toluenesulfonic acid → HCID 90028018, compound

HRID 1506949Notes

Reaction equation

HRID 1506949 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([OH:16])[C@H:9]([OH:15])[CH2:10][O:11]COC.CO[C:19](OC)([CH3:21])[CH3:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[O:16][C:19]([CH3:21])([CH3:20])[O:15][C@@H:9]1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 118151924HCID 118151924, compound

Product 1

HCID 90028018HCID 90028018, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To (1R,2R)-1-(2-chlorophenyl)-3-(methoxymethoxy)propane-1,2-diol (3.31 g, 13.4 mmol, Preparation example 3), Dichloromethane was added and cooled to 0° C. 2,2-Dimethoxypropane (3.3 ml, 26.8 mmol) and p-toluenesulfonic acid (2 g, 10.7 mmol) was added and stirred at room temperature for 5 hrs. The reaction mixture was quenched with H2O, extracted with DCM, and washed with H2O. The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated. The crude compound was purified by a silica gel column to produce the title compound (1.05 g, 30˜40%).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted with DCM
  3. washwashed with H2O
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-e15a311267d347e38ff4ff3404227d24
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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