p-Toluenesulfonic acid → (S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol

HRID 705320Notes

Reaction equation

HRID 705320 reaction equation
[Cl:1][CH2:2][C@@H:3]([OH:27])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:15]2[CH:26]=[CH:25][C:18]([O:19][CH2:20][C@H:21]([OH:24])[CH2:22][OH:23])=[CH:17][CH:16]=2)([CH3:14])[CH3:13])=[CH:8][CH:7]=1.CO[C:30](OC)([CH3:32])[CH3:31].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Cl:1][CH2:2][C@@H:3]([OH:27])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([C:15]2[CH:16]=[CH:17][C:18]([O:19][CH2:20][C@H:21]3[CH2:22][O:23][C:30]([CH3:32])([CH3:31])[O:24]3)=[CH:25][CH:26]=2)([CH3:14])[CH3:13])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 45107537Ralaniten

Product 1

HCID 117689849(S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (R)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propane-1,2-diol (1000 mg, 2.53 mmol) in acetone (8.0 mL) was added 2,2-dimethoxypropane (630 μL, 5.06 mmol) and catalytic amounts of p-toluenesulfonic acid. After 14 h, the reaction mixture was quenched with an aqueous solution of sodium chloride and stirred for 15 min, and the resulting mixture was extracted twice with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate and filtered. Solvents were evaporated, and the resulting crude material was purified by silica gel flash chromatography (eluent: 2% methanol in dichloromethane) to provide the title compound.

Workup

  1. customthe reaction mixture was quenched with an aqueous solution of sodium chloride
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customSolvents were evaporated
  6. customthe resulting crude material was purified by silica gel flash chromatography (eluent: 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-bb0d4f115dbf413186d79f71c4bc229d
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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