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

HRID 2280614

反応式

HRID 2280614 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4da8b961396b41438095f60fc36f0b12
出典データセット
uspto-grants-2015_09
特許番号
US09139536B2

関連ノート

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