Water → HCID 58604070, compound

HRID 2113673Notes

Reaction equation

HRID 2113673 reaction equation
[CH2:1]([C:4]1([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([F:17])=[C:9]([O:15][CH3:16])[C:10]=2[Cl:14])[C:5]1=[O:18])[CH:2]=[CH2:3].C1(=O)C=CC(=[O:29])C=C1.O.Cl(O)(=O)(=O)=O>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:19]([C:4]1([CH2:1][C:2](=[O:29])[CH3:3])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([F:17])=[C:9]([O:15][CH3:16])[C:10]=2[Cl:14])[C:5]1=[O:18])[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 4650QuinoneHCID 24247Perchloric AcidHCID 58604049HCID 58604049, compound

Product 1

HCID 58604070HCID 58604070, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

2-allyl-2-butyl-5-chloro-7-fluoro-6-methoxy-3,4-dihydro-2H-naphthalen-1-one (40 mg, 0.12 mmol) was dissolved in acetonitrile (0.36 mL) and treated with benzoquinone (20 mg, 0.18 mmol), Pd(OAc)2 (5 mg. 0.02 mmol), water (0.018 mL) and perchloric acid (70%, 0.005 mL) to give an orange solution. This solution was stirred under an air atmosphere for 16.5 hours, then purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.), developing with 4:1 hexane-EtOAc. The band at Rf 0.53-0.59 was eluted with 5% MeOH in CH2Cl2 to give 2-butyl-5-chloro-7-fluoro-6-methoxy-2-(2-oxopropyl)-3,4-dihydro-2H-naphthalen-1-one as a slightly yellow oil.

Workup

  1. customto give an orange solution
  2. custompurified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.)
  3. washThe band at Rf 0.53-0.59 was eluted with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-f3b9dd35826b4400a9e0b1a0fd2c1f58
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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