Dichloromethane → HCID 22490823, compound

HRID 2180621Notes

Reaction equation

HRID 2180621 reaction equation
[Br: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](/[CH:22]([CH3:24])[CH3:23])=[C:18](/[F:21])\[CH2:19][OH:20])[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]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4](/[C:17](/[CH:22]([CH3:24])[CH3:23])=[C:18](/[F:21])\[CH:19]=[O:20])[C:3]=1[O:25][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 82029Methyl morpholine oxideHCID 22491029HCID 22491029, compound2×

Product 1

HCID 22490823HCID 22490823, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

As described in General Procedure H-1, (2E)-3-(4-bromo-3-ethoxy-8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-2-fluoro-4-methyl-pent-2-en-1-ol (Compound A-138, 140 mg, 0.32 mmol), tetrapropylammonium perruthenate (10 mg, 0.028 mmol) and 4 methylmorpholine N-oxide (94 mg, 0.80 mmol) were reacted in acetonitrile and dichloromethane to give the title compound as a white solid after purification by flash column chromatography (silica gel, 5% ethyl acetate in hexane).

Sources & evidence

ORD record
ord-283b368740ce48469604280ac01ea483
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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