Diethyl Ether → HCID 22218230, compound

HRID 1795588Notes

Reaction equation

HRID 1795588 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=O)[CH2:8][CH2:7][C:6]2([CH3:16])[CH3:15].C[Mg+].[Br-].[CH2:20](OCC)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10]([C:9]([CH3:20])=[CH:8][CH2:7][C:6]2([CH3:16])[CH3:15])=[CH:11][C:12]=1[CH3:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 22218197HCID 22218197, compound2×HCID 178418689HCID 178418689, compound

Product 1

HCID 22218230HCID 22218230, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

General Procedure F CeCl3.7H2O (2.6 g, 6.9 mmol) was heated in an oil bath at 140-150° C. under high vacuum without stirring for 1 h, and then with stirring for 2 h. Argon was then introduced, and the flask was cooled to room temperature. Tetrahydrofuran (15 mL) was added, and the resulting slurry solution was stirred at room temperature under the argon atmosphere for 16 h. A solution of 6-methoxy-4,4,7-trimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound 30, 1.0 g, 4.6 mmol) and 5 mL of tetrahydrofuran was added, and the reaction mixture was stirred for 1 h, then cooled to 0° C. A solution of 3 M MeMgBr in diethyl ether (2.3 mL, 6.9 mmol) was added, and the ice bath was removed. After 1 h, the reaction was poured into concentrated sulfuric acid in ice, extracted with ethyl acetate, washed with NaHCO3 1 N, brine, dried over MgSO4, and filtered. The solvent was removed to give 1.0 g (100%) of the title compound as an orange oil. PNMR (300 MHz, CDCl3) δ 1.52 (s, 6 H), 2.28 (s, 3 H), 2.42 (d, 2 H, J=3.4 Hz), 2.49 (s, 1 H), 4.07 (s, 3 H), 5.86 (t, 1 H, J=2.5 Hz), 7.08 (s, 1 H), 7.30 (s, 1 H). 4-Ethyl-7-methoxy-1,1,6-trimethyl-1,2-dihydro-naphthalene (Compound 32)

Workup

  1. stirringwith stirring for 2 h
  2. additionArgon was then introduced
  3. stirringthe resulting slurry solution was stirred at room temperature under the argon atmosphere for 16 h
  4. stirringthe reaction mixture was stirred for 1 h
  5. temperaturecooled to 0° C
  6. customthe ice bath was removed
  7. waitAfter 1 h
  8. additionthe reaction was poured into concentrated sulfuric acid in ice
  9. extractionextracted with ethyl acetate
  10. washwashed with NaHCO3 1 N, brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. customThe solvent was removed

Sources & evidence

ORD record
ord-e85f6e944a114c209ee2fc48179e49d3
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

Loading…