Water → (S)-3-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxy)-propane-1,2-diol

HRID 882926Notes

Reaction equation

HRID 882926 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:29]=[CH:28][C:8]([O:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:27]=[CH:26][C:16]([O:17][CH2:18][C@@H:19]3[CH2:23][O:22]C(C)(C)[O:20]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:27]=[CH:26][C:16]([O:17][CH2:18][C@@H:19]([OH:20])[CH2:23][OH:22])=[CH:15][CH:14]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67029042(R)-4-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxymethyl)-2,2-dimethyl-[1,3]dioxolane

Product 1

HCID 67028182(S)-3-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxy)-propane-1,2-diol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-4-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxymethyl)-2,2-dimethyl-[1,3]dioxolane (5.0 g, 10.8 mmol) in DCM (50 mL) is added TFA (2.0 mL, 26.9 mmol) dropwise followed by water (2.0 mL) and the reaction mixture is stirred at RT overnight. The solvent is removed in vacuo and the residue is treated with aqueous sodium hydrogen carbonate solution. The mixture is extracted with EtOAc (3×200 mL) and the combined organic portions are washed with water, brine, dried over Na2SO4 and concentrated in vacuo. Recrystallizisation of the residue from diethyl ether-hexane affords the title compound as white solid.

Workup

  1. customThe solvent is removed in vacuo
  2. additionthe residue is treated with aqueous sodium hydrogen carbonate solution
  3. extractionThe mixture is extracted with EtOAc (3×200 mL)
  4. washthe combined organic portions are washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-752ea989c16b46fb824c2631434aeb73
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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