Methyl vinyl ketone → 2-butyl-6-methoxy-2-(3-oxobutyl)-3,4-dihydro-1(2H)-naphthalenone

HRID 2113677

Reaction equation

HRID 2113677 reaction equation
[CH2:1]([CH:5]1[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:17])[CH2:2][CH2:3][CH3:4].N12CCCN=C1CCCCC2.[CH:29]([C:31]([CH3:33])=[O:32])=[CH2:30]>O1CCCC1>[CH2:1]([C:5]1([CH2:30][CH2:29][C:31](=[O:32])[CH3:33])[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:17])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketone2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 586040732-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 586040682-butyl-6-methoxy-2-(3-oxobutyl)-3,4-dihydro-1(2H)-naphthalenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone (230 mg, 1 mmol) in anhydrous tetrahydrofuran (THF, 0.5 mL) was placed under a N2 atmosphere and treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.037 mL, 0.25 mmol) followed by methyl vinyl ketone (MVK, 0.104 mL, 1.25 mmol). The mixture was stirred at room temperature for 19 hours and then heated at 60° C. for 80 minutes. Additional MVK (0.104 mL, 1.25 mmol) was added and the mixture was stirred at 60° C. for 2.5 hours. Additional DBU (0.037 mL, 0.25 mmol) was then added and the mixture was stirred at 60° C. for 70 minutes. After cooling to room temperature, the mixture was concentrated under a stream of N2 and the residue was purified by preparative layer chromatography on three 0.1×20×20 cm silica gel GF plates (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 2-butyl-6-methoxy-2-(3-oxobutyl)-3,4-dihydro-1(2H)-naphthalenone as an oil.

Workup

  1. temperatureheated at 60° C. for 80 minutes
  2. stirringthe mixture was stirred at 60° C. for 2.5 hours
  3. stirringthe mixture was stirred at 60° C. for 70 minutes
  4. temperatureAfter cooling to room temperature
  5. concentrationthe mixture was concentrated under a stream of N2
  6. customthe residue was purified by preparative layer chromatography on three 0.1×20×20 cm silica gel GF plates (Analtech, Newark, Del.)
  7. washThe UV visible product band was eluted with EtOAc
  8. customthe eluant was evaporated under vacuum

Sources & evidence

ORD record
ord-36175f51c07c45aca472c822f4c3a0d5
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Linked notes

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