Methyl morpholine oxide → HCID 73989338, compound

HRID 2180576Notes

Reaction equation

HRID 2180576 reaction equation
[CH2:1]([O:3][C:4]1[C:5](/[C:16](/[CH3:21])=[C:17](/[F:20])\[CH2:18][OH:19])=[CH:6][C:7]2[CH:8]=[CH:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)[CH3:2].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([O:3][C:4]1[C:5]([C:16]([CH3:21])=[C:17]([F:20])[CH:18]=[O:19])=[CH:6][C:7]2[CH:8]=[CH:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22490958HCID 22490958, compound

Product 1

HCID 73989338HCID 73989338, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (2E)-3-(3-ethoxy-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-2-fluoro-but-2-en-1-ol (Compound A-49, 18 mg, 0.06 mmol), 4 Å molecular sieves (0.1 g) in dichloromethane (3 mL) was treated with tetrapropylammonium perruthenate (10 mg, 0.028 mmol) and 4 methylmorpholine N-oxide (15 mg, 0.12 mmol). The solution was stirred under argon for 30 min and filtered through a silica gel plug (20% ethyl acetate in hexanes). The filtrate was concentrated under vacuum to give the title compound.

Workup

  1. filtrationfiltered through a silica gel plug (20% ethyl acetate in hexanes)
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a9f6cebb935f47489158c900d625720e
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

Loading…