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

HRID 2221303ノート

反応式

HRID 2221303 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6212Chloroform溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-47ce150fca68458cbc16cb9fe092bc1d
出典データセット
uspto-grants-2008_05
特許番号
US07368567B2

反応ノート

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