Dichloromethane → (E)-3-(3-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enal

HRID 1744907Notes

Reaction equation

HRID 1744907 reaction equation
[CH2:1]([O:3][C:4]1[C:5](/[C:18](/[CH2:23][CH3:24])=[C:19](/[F:22])\[CH2:20][OH:21])=[CH:6][C:7]2[C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)[CH3:2].ClCCl.C([N+](CCC)(CCC)CCC)CC.C[N+]1([O-])CCOCC1>C(#N)C>[CH2:1]([O:3][C:4]1[C:5](/[C:18](/[CH2:23][CH3:24])=[C:19](/[F:22])\[CH:20]=[O:21])=[CH:6][C:7]2[C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][C:11]([CH3:14])([CH3:15])[C:12]=2[CH:13]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 69591056(E)-3-(3-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enol

Product 1

HCID 86593750(E)-3-(3-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enal

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (E)-3-(3-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enol (3.55 g, 8.02 mmol) and dichloromethane (125 mL) in acetonitrile (25 mL) was treated with tetrapropylammonium peruthenate (0.476 g, 1.45 mmol), 4 Å molecular sieves (0.442 g), and N-methylmorpholine-N-oxide (2.78 g, 23.8 mmol), and the mixture was stirred for 0.5 h at ambient temperature. The solution was filtered through a sintered glass funnel containing a bed of silica gel about 1 inch thick using 20% ethyl acetate in hexane as the eluent. The solvent was removed in vacuo to give the title compound.

Workup

  1. filtrationThe solution was filtered through a sintered glass funnel
  2. additioncontaining a bed of silica gel about 1 inch
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e18e6bb259ab4b5f8466fedfe9f8fc1f
Source dataset
uspto-grants-2006_03
Patent number
US07019034B2

Reaction notes

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