Dichloromethane → HCID 22491057, compound

HRID 2180625Notes

Reaction equation

HRID 2180625 reaction equation
[Cl:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4](/[C:17](/[CH3:22])=[C:18](/[F:21])\[CH2:19][OH:20])[C:3]=1[O:23][CH2:24][CH3:25].C[N+]1([O-])CCOCC1.ClCCl>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4](/[C:17](/[CH3:22])=[C:18](/[F:21])\[CH:19]=[O:20])[C:3]=1[O:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 82029Methyl morpholine oxideHCID 22490906HCID 22490906, compound

Product 1

HCID 22491057HCID 22491057, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

As described in General Procedure H-1, (2E)-3-(4-chloro-3-ethoxy-8-isopropyl-5,5-dimethyl-5,6-dihydronaphthalen-2-yl)-2-fluoro-but-2-en-1-ol (Compound A-144, 0.18 g, 0.49 mmol), tetrapropylammonium perruthenate (25 mg, 0.071 mmol) and 4-methylmorpholine N-oxide (115 mg, 0.98 mmol) were reacted in acetonitrile and dichloromethane to give the title compound after purification by flash column chromatography (silica gel, 10% ethyl acetate in hexanes).

Sources & evidence

ORD record
ord-899d24a905f84e8faaa535c57741e49d
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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