Dichloromethane → HCID 22490819, compound

HRID 2180624Notes

Reaction equation

HRID 2180624 reaction equation
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH2:16][CH3:17])[CH3:15])[C:6]=2[CH:5]=[C:4](/[C:18](/[CH2:23][CH3:24])=[C:19](/[F:22])\[CH2:20][OH:21])[C:3]=1[O:25][CH2:26][CH3:27].C[N+]1([O-])CCOCC1.ClCCl>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH2:16][CH3:17])[CH3:15])[C:6]=2[CH:5]=[C:4](/[C:18](/[CH2:23][CH3:24])=[C:19](/[F:22])\[CH:20]=[O:21])[C:3]=1[O:25][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 82029Methyl morpholine oxideHCID 22490772HCID 22490772, compound

Product 1

HCID 22490819HCID 22490819, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

As described in General Procedure H-1, (2E)-3-(4-bromo-8-sec-butyl-3-ethoxy-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-2-fluoro-pent-2-en-1-ol (Compound A-143, 411 mg, 0.94 mmol), tetrapropylammonium perruthenate (10 mg, 0.028 mmol) and 4-methylmorpholine N-oxide (274 mg, 2.34 mmol) were reacted in acetonitrile and dichloromethane to give the title compound as a yellow oil after purification by flash column chromatography (silica gel, 5% ethyl acetate in hexane).

Sources & evidence

ORD record
ord-806a4bed86a34d36a294b7d5048d73b8
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

Loading…