Water → HCID 58869145, compound

HRID 2355214Notes

Reaction equation

HRID 2355214 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C@@H:18]([OH:21])[CH2:19][OH:20])=[C:12](Br)[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]1([S:7]([C:10]2[CH:15]=[C:14]3[C:13]([CH2:16][CH2:17][C@H:18]([CH2:19][OH:20])[O:21]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 66917418HCID 66917418, compound

Product 1

HCID 58869145HCID 58869145, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-4-(4-benzenesulfonyl-2-bromo-phenyl)-butane-1,2-diol (1.71 g) in THF (15 mL) were added palladium acetate (30 mg), racemic 2[P(t-Bu)2]-1,1-binaphthyl (53.1 mg) and K3PO4 (1.42 g) under Argon atmosphere. The reaction was heated at reflux for 48 hours; then water was added and the mixture was extracted 3 times with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash chromatography (hexane/EtOAc, 6/4) to afford ((R)-7-benzenesulfonyl-chroman-2-yl)-methanol (1.20 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 48 hours
  3. extractionthe mixture was extracted 3 times with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via flash chromatography (hexane/EtOAc, 6/4)

Sources & evidence

ORD record
ord-4fdb97d3fbe3419eb5fb3f734436510d
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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