Diethylamine → 2,2-Diethyl-4-methoxy-1a,2,7,7a-tetrahydro-1H-naphtho[2,3-b]azirene

HRID 1760726Notes

Reaction equation

HRID 1760726 reaction equation
[CH2:1]([C:3]1([CH2:17][CH3:18])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5][C:4]1=[N:15]O)[CH3:2].C(NCC)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([C:3]1([CH2:17][CH3:18])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH:5]2[NH:15][CH:4]12)[CH3:2]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 21226445Aluminium lithium hydrideHCID 59925106HCID 59925106, compound

Product 1

HCID 159230752,2-Diethyl-4-methoxy-1a,2,7,7a-tetrahydro-1H-naphtho[2,3-b]azirene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,1-Diethyl-7-methoxy-3,4-dihydro-1H-naphthalen-2-one oxime (4.68 g, 18.96 mmol) in dry THF (100 mL) at 0° C. was added the diethylamine (4.9 mL, 47.4 mmol) and the LAH (95% powder) (2.16 g, 56.9 mmol). The mixture was stirred at 0° C. for min then heated to reflux for 3 h. The gray solution was cooled down to 0° C., quenched with brine and diluted with AcOEt. The organic layer was decanted, washed with H2O (2×), brine, dried over MgSO4, filtered then evaporated. The residue was purified by a flash chromatography (3% MeOH/CH2Cl2) (3.889 g, 89%).

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 3 h
  3. temperatureThe gray solution was cooled down to 0° C.
  4. customquenched with brine
  5. additiondiluted with AcOEt
  6. customThe organic layer was decanted
  7. washwashed with H2O (2×), brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customthen evaporated
  11. customThe residue was purified by a flash chromatography (3% MeOH/CH2Cl2) (3.889 g, 89%)

Sources & evidence

ORD record
ord-095d0118bf8147cd8e4bc85b6a696076
Source dataset
uspto-grants-2005_01
Patent number
US06844368B1

Reaction notes

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