Lithium Bromide → HCID 66917128, compound

HRID 1183035Notes

Reaction equation

HRID 1183035 reaction equation
[CH3:1][C:2]1([CH3:23])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17]OS(C)(=O)=O)=[CH:11][CH:10]=2)[CH2:4][O:3]1.[Br-:24].[Li+]>CC(C)=O>[Br:24][CH2:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C@@H:5]2[CH2:4][O:3][C:2]([CH3:23])([CH3:1])[O:6]2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 86641908Methanesulfonic acid 3-[4-((R)-2,2-dimethyl[1,3]dioxolan-4-ylmethoxy)-phenyl]-propylester

Product 1

HCID 66917128HCID 66917128, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methanesulfonic acid 3-[4-((R)-2,2-dimethyl[1,3]dioxolan-4-ylmethoxy)-phenyl]-propylester (11.8 g, 34.2 mmol) in acetone (200 mL) is treated with lithium bromide (8.9 g, 100 mmol) and then heated to reflux for 5 h. After cooling to RT the mixture is concentrated in vacuo. The resulting residue is dissolved in EtOAc (150 mL), washed with water (2×50 mL), brine then dried (MgSO4), filtered and concentrated in vacuo to give an oil. Purification by flash chromatography (SiO2, iso-hexane:EtOAc, 4:1) gives the title compound as colourless oil that solidifies upon standing.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 h
  3. concentrationis concentrated in vacuo
  4. dissolutionThe resulting residue is dissolved in EtOAc (150 mL)
  5. washwashed with water (2×50 mL), brine
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an oil
  10. customPurification by flash chromatography (SiO2, iso-hexane:EtOAc, 4:1)

Sources & evidence

ORD record
ord-2a66b794847e4218801cba49d6a4523f
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

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