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

HRID 33949

Reaction equation

HRID 33949 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-765e7f3a30eb460182dadf93c7120c6d
Source dataset
uspto-grants-2008_09
Patent number
US07429681B2

Linked notes

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