1,4-Dioxane--water (1/1) → 5-Isopropoxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one

HRID 1944636

反応式

HRID 1944636 の反応式
[CH:1]([O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10]2)([CH3:3])[CH3:2].O.[O:18]1CCOCC1>O1CCOCC1>[CH:1]([O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][C:10]2=[O:18])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 218864351,4-Dioxane--water (1/1)HCID 574359005-Isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene

生成物 1

HCID 574359025-Isopropoxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one収率 71%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

34 (120 mg, 0.55 mmol) was weighed in a 100 mL round bottom flask and a solution of 5 mL of water:dioxane (5:95) was added and the reaction was set up under nitrogen. A solution of 2,4-dichloro-5,6-dicyanobenzoquinone (0.25 g, 1.09 mmol) dissolved in 5 mL of dioxane was added dropwise to the reaction mixture. The reaction mixture was stirred for 12 h. The solid separated was filtered and washed with ethylacetate. The filtrate was concentrated under reduced pressure and 10 mL of saturated sodium bicarbonate solution was added and the resulting reaction mixture was extracted with ether (3×20 mL) and the combined organic phases dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. Purification by flash column chromatography (silica gel, 30:70 EtOAc:Hexanes) yielded 90 mg (71%) of 35. Rf value: 0.458 (40:60 EtOAc:Hexanes).

後処理

  1. additionwas added dropwise to the reaction mixture
  2. customThe solid separated
  3. filtrationwas filtered
  4. washwashed with ethylacetate
  5. concentrationThe filtrate was concentrated under reduced pressure and 10 mL of saturated sodium bicarbonate solution
  6. additionwas added
  7. customthe resulting reaction mixture
  8. extractionwas extracted with ether (3×20 mL)
  9. dry with materialthe combined organic phases dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customPurification by flash column chromatography (silica gel, 30:70 EtOAc:Hexanes)

出典と根拠

ORDレコード
ord-af98ecb8645b4e65b56328bb4228a866
出典データセット
uspto-grants-2013_03
特許番号
US08394859B2

関連ノート

読み込み中…