Hydrochloric Acid → 5-bromo-1-(1,3-dithian-2-yl)-2,3-dihydro-1H-inden-1-ol

HRID 2360042

반응식

HRID 2360042 반응식
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH2:2]1.C([Li])CCC.[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[CH2:17][CH2:16]2.Cl>O1CCCC1>[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18]([CH:2]1[S:3][CH2:4][CH2:5][CH2:6][S:1]1)([OH:22])[CH2:17][CH2:16]2

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 104511,3-DithianeHCID 5206955-Bromo-1-indanoneHCID 178418339Butyllithium

생성물 1

HCID 574194845-bromo-1-(1,3-dithian-2-yl)-2,3-dihydro-1H-inden-1-ol수율 100%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-15 °C

실험 절차

A solution of 1,3-dithiane (11.96 g, 99 mmol) in anhydrous tetrahydrofuran (100 mL) at −30° C. was treated dropwise over 10 min with n-butyllithium (2.5M in hexanes, 38.4 mL, 96 mmol) followed by stirring at −15° C. for 2 h. The solution was then treated with a solution of 5-bromo-2,3-dihydro-1H-inden-1-one (15 g, 71.1 mmol) in anhydrous tetrahydrofuran (250 mL) over 1 h, maintaining the temperature between −9° C. and 2° C. The mixture was then allowed to set in the refrigerator at 2-8° C. for 18 h. The solution was concentrated in vacuo to afford a maroon oil, which was treated with 1 N hydrochloric acid solution and extracted with ether. The ether layer was extracted with saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo to afford an amber oil (23.55 g).

후처리

  1. temperaturemaintaining the temperature between −9° C. and 2° C
  2. waitto set in the refrigerator at 2-8° C. for 18 h
  3. concentrationThe solution was concentrated in vacuo
  4. customto afford a maroon oil, which
  5. extractionextracted with ether
  6. extractionThe ether layer was extracted with saturated sodium chloride solution
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-18f481ce83cf46cd9634be1edba1d8be
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685991B2

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