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

HRID 1944636

반응식

HRID 1944636 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-af98ecb8645b4e65b56328bb4228a866
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394859B2

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