Dichloromethane → HCID 22490914, compound

HRID 2180623Notes

Reaction equation

HRID 2180623 reaction equation
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4](/[C:18](/[CH3:23])=[C:19](/[F:22])\[CH2:20][OH:21])[C:3]=1[O:24][CH2:25][CH3:26].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]([C:14]([CH3:15])([CH3:16])[CH3:17])[C:6]=2[CH:5]=[C:4](/[C:18](/[CH3:23])=[C:19](/[F:22])\[CH:20]=[O:21])[C:3]=1[O:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 82029Methyl morpholine oxideHCID 22491004HCID 22491004, compound

Product 1

HCID 22490914HCID 22490914, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

As described in General Procedure H-1, (2E)-3-(4-bromo-8-tert-butyl-3-ethoxy-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-2-fluoro-but-2-en-1-ol (Compound A-141, 45 mg, 0.11 mmol), tetrapropylammonium perruthenate (10 mg, 0.028 mmol) and 4-methylmorpholine N-oxide (31 mg, 0.26 mmol) were reacted in acetonitrile and dichloromethane to give the title compound after purification by flash column chromatography (silica gel, 5% ethyl acetate in hexane).

Sources & evidence

ORD record
ord-f12646d6ae7f47449b1b4c1e1c1a0165
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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