Acetic Acid → 10a-butyl-7-methoxy-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone

HRID 2113678Notes

Reaction equation

HRID 2113678 reaction equation
[CH2:1]([C:5]1([CH2:18][CH2:19][C:20](=[O:22])[CH3:21])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[C:6]1=O)[CH2:2][CH2:3][CH3:4].N1CCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([C:5]12[CH2:18][CH2:19][C:20](=[O:22])[CH:21]=[C:6]1[C:7]1[C:12](=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=1)[CH2:13][CH2:14]2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 586040682-butyl-6-methoxy-2-(3-oxobutyl)-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 5860405910a-butyl-7-methoxy-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-butyl-6-methoxy-2-(3-oxobutyl)-3,4-dihydro-1(2H)-naphthalenone (91 mg, 0.3 mmol), pyrrolidine (0.025 mL, 0.3 mol), acetic acid (0.017 mL, 0.3 mmol), and toluene (0.5 mL) was stirred and heated in an oil bath at 100° C. for 3 hours. After standing at room temperature overnight, the mixture was partitioned between EtOAc (20 mL) and water (20 mL) containing 2N HCl (2 mL). The organic phase was washed with 5% NaHCO3 (10 mL) and brine (10 mL), dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.), developing with 5% EtOAc in CH2Cl2. The UV visible product band was eluted with EtOAc and the eluant was evaporated under vacuum to provide 10a-butyl-7-methoxy-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone as a clear oil.

Workup

  1. customthe mixture was partitioned between EtOAc (20 mL) and water (20 mL)
  2. additioncontaining 2N HCl (2 mL)
  3. washThe organic phase was washed with 5% NaHCO3 (10 mL) and brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.)
  8. washThe UV visible product band was eluted with EtOAc
  9. customthe eluant was evaporated under vacuum

Sources & evidence

ORD record
ord-f1104594af664bcb8d15577b9ef1cd47
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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