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

HRID 617695노트

반응식

HRID 617695 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-56454dfac1fa490fa8a4d7f70b538678
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952266

반응 노트

불러오는 중…