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

HRID 1744914Notes

Reaction equation

HRID 1744914 reaction equation
[CH2:1]([O:4][C:5]1[C:6](/[C:19](/[CH2:24][CH3:25])=[C:20](/[F:23])\[CH2:21][OH:22])=[CH:7][C:8]2[C:9]([CH3:18])([CH3:17])[CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1)[CH2:2][CH3:3].C([N+](CCC)(CCC)CCC)CC.C[N+]1([O-])CCOCC1>ClCCl.C(#N)C>[CH2:1]([O:4][C:5]1[C:6](/[C:19](/[CH2:24][CH3:25])=[C:20](/[F:23])\[CH:21]=[O:22])=[CH:7][C:8]2[C:9]([CH3:17])([CH3:18])[CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 22226108HCID 22226108, compound

Product 1

HCID 22226104(E)-3-(3-Propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enal

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-3-(3-propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enol (2.05 g, 6.13 mmol) in dichloromethane (81 mL) and acetonitrile (16 mL) was treated with tetrapropylammonium peruthenate (0.305 g, 0.92 mmol), 4 Å molecular sieves (0.442 g), and N-methylmorpholine-N-oxide (2.41 g, 15.3 mmol), and the solution was stirred for 0.5 h at ambient temperature. The mixture 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 mixture 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-215b0224659648f796c7cf1aa6c4a6ea
Source dataset
uspto-grants-2006_03
Patent number
US07019034B2

Reaction notes

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