Potassium Hydroxide → (7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-yl)-methanol

HRID 2221303Notes

Reaction equation

HRID 2221303 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([O:19][CH2:20][C@@H:21]3[CH2:23][O:22]3)=[C:14](C(=O)C)[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:29].[OH-].[K+]>C(Cl)(Cl)Cl.CO>[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:19][CH2:20][C@@H:21]([CH2:23][OH:22])[O:29][C:14]=3[CH:15]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 866015571-(5-benzenesulfonyl-2-(S)-oxiranylmethoxy-phenyl)-ethanone

Product 1

HCID 59710879(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-yl)-methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of 1-(5-benzenesulfonyl-2-(S)-oxiranylmethoxy-phenyl)-ethanone (2.04 g; 0.059 mol) and meta-chloroperoxybenzoic acid (4.13 g; 0.018 mol, max. 77%) in chloroform (20 mL) was heated under reflux for 18 hours. After cooling to ambient temperature the mixture was diluted with chloroform, filtered, washed with water and saturated sodium bicarbonate, dried (Na2SO4) and concentrated in vacuo. This crude residue (0.85 g; 0.0024 mol) dissolved in methanol (5 mL) was added to a solution of 10% aqueous potassium hydroxide (4 mL) at 0° C. The mixture was stirred for 30 minutes at room temperature. Solvent was removed in vacuo, and the residue was dissolve in ethyl acetate, washed with 10% aqueous hydrochloric acid followed by saturated brine, dried (Na2SO4) and concentrated in vacuo to give (7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-yl)-methanol as an oil (1.44 g; 77%): MS (M+H)+ 307.

Workup

  1. temperatureunder reflux for 18 hours
  2. filtrationfiltered
  3. washwashed with water and saturated sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customSolvent was removed in vacuo
  7. dissolutionthe residue was dissolve in ethyl acetate
  8. washwashed with 10% aqueous hydrochloric acid
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47ce150fca68458cbc16cb9fe092bc1d
Source dataset
uspto-grants-2008_05
Patent number
US07368567B2

Reaction notes

Loading…