Dichloromethane → HCID 22491039, compound

HRID 2180622Notes

Reaction equation

HRID 2180622 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](/[CH3:22])=[C:18](/[F:21])\[CH2:19][OH:20])[C:3]=1[O:23][CH:24]([CH3:26])[CH3:25].C([N+](CCC)(CCC)CCC)CC.C[N+]1([O-])CCOCC1.ClCCl>C(#N)C>[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](/[CH3:22])=[C:18](/[F:21])\[CH:19]=[O:20])[C:3]=1[O:23][CH:24]([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 22491003HCID 22491003, compound

Product 1

HCID 22491039HCID 22491039, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

As described in General Procedure H-1, (2E)-3-(4-bromo-3-isopropoxy-8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-2-fluoro-but-2-en-1-ol (Compound A-139, 220 mg, 0.52 mmol), tetrapropylammonium peruthenate (10 mg, 0.028 mmol) and 4-methylmorpholine N-oxide (151 mg, 1.25 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-f50b2015850e4206ad8d4b4fdf580a66
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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