Ethylene Glycol → 6-bromo-2,3-dihydrospiro[4H-1-benzothiopyran-4,2'-[1,3]dioxolane]

HRID 617695ノート

反応式

HRID 617695 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][CH2:8][C:7](=[O:11])[C:6]=2[CH:12]=1.[CH2:13](O)[CH2:14][OH:15]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][CH2:8][C:7]3([O:15][CH2:14][CH2:13][O:11]3)[C:6]=2[CH:12]=1

参加物

5

反応物 2

HCID 174Ethylene GlycolHCID 139537366-Bromo-2,3-dihydro-4H-1-benzothiopyran-4-one

生成物 1

HCID 218490186-bromo-2,3-dihydrospiro[4H-1-benzothiopyran-4,2'-[1,3]dioxolane]収率 78.8%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 1140Toluene溶媒

実験手順

14.7 g (0.060 mol) of the title compound of Step B, 11 mL (0.19 mol) of ethylene glycol (purchased from Aldrich Chemical Company), and 0.4 g (2.10 mmol) of p-toluenesulfonic acid monohydrate (purchased from Aldrich Chemical Company) were added to 125 mL of toluene. The solution was stirred at reflux under nitrogen overnight, and was then washed with 1M sodium carbonate (2×250 mL), followed by water (2×250 mL). The organic layer was dried (Na2SO4), filtered, and evaporated to dryness to yield 13.58 g of the title compound of Step C as an oil. 1H NMR (CDCl3): δ2.2 (m,2H), 3.16 (m,2H), 4.1 (m,2H), 4.2 (m,2H), 7.0-7.6 (3H).

後処理

  1. temperatureat reflux under nitrogen overnight
  2. washwas then washed with 1M sodium carbonate (2×250 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-56454dfac1fa490fa8a4d7f70b538678
出典データセット
uspto-grants-1999_09
特許番号
US05952266

反応ノート

読み込み中…