6-Methoxy-alpha-tetralone → HCID 11831424, compound

HRID 370011Notes

Reaction equation

HRID 370011 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17](=O)[CH2:16][CH2:15][CH2:14]2.[Cl-].[NH4+]>C(OCC)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:16][CH2:15][CH2:14]2

Participants

5

Reactant 3

HCID 141126-Methoxy-alpha-tetraloneHCID 25517Ammonium ChlorideHCID 178418255HCID 178418255, compound2×

Product 1

HCID 11831424HCID 11831424, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of phenylmagnesium bromide in diethyl ether (3.0 M, 23 mL, 69 mmol) was added dropwise to a solution of 6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one 27 (10.0 g, 56.7 mmol) in diethyl ether (100 mL) at room temperature. The reaction mixture was heated at reflux for 1.5 h. An additional portion of phenylmagnesium bromide solution (10 mL, 60 mmol) was added to the cooled reaction mixture, and the resultant mixture was heated at reflux for an additional 2.5 h. The cooled mixture was poured into a saturated solution of ammonium chloride (200 mL), and stirred for 15 min. The organic layer was separated, washed with a saturated solution of sodium chloride, and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the resultant oil was treated with a solution of sulfuric acid (8 mL) in acetic acid (30 mL) at room temperature for 1.5 h. Ice water (300 mL) was added to the solution, and the product was extracted into dichloromethane (200 mL), washed with water, and a saturated aqueous solution of sodium bicarbonate, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by medium pressure chromatography using ethyl acetate 0 to 3% in hexanes as the eluent, to give the 6-methoxy-1-phenyl-3,4-dihydronaphthalene 28 in two crops 4.0 g (29%) and an impure fraction 5.02 g (37%) as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 h
  3. temperatureat reflux for an additional 2.5 h
  4. customThe organic layer was separated
  5. washwashed with a saturated solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. additionthe resultant oil was treated with a solution of sulfuric acid (8 mL) in acetic acid (30 mL) at room temperature for 1.5 h
  9. additionIce water (300 mL) was added to the solution
  10. extractionthe product was extracted into dichloromethane (200 mL)
  11. washwashed with water
  12. dry with materiala saturated aqueous solution of sodium bicarbonate, and dried over magnesium sulfate
  13. customThe solvent was evaporated in vacuo
  14. customthe residue was purified by medium pressure chromatography

Sources & evidence

ORD record
ord-c18a0fc81074453cad553f628f179da1
Source dataset
uspto-grants-2000_10
Patent number
US06140354

Reaction notes

Loading…