Methyl morpholine oxide → (E)-2-Fluoro-3-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enal

HRID 1883269Notes

Reaction equation

HRID 1883269 reaction equation
[F:1]/[C:2](=[C:5](/[C:8]1[C:17]([O:18][CH2:19][CH2:20][CH3:21])=[CH:16][C:15]2[C:14]([CH3:23])([CH3:22])[CH2:13][CH2:12][C:11]([CH3:25])([CH3:24])[C:10]=2[CH:9]=1)\[CH2:6]C)/[CH2:3][OH:4].C[N+]1([O-])CCOCC1>C(Cl)Cl.CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[F:1]/[C:2](=[C:5](/[C:8]1[C:17]([O:18][CH2:19][CH2:20][CH3:21])=[CH:16][C:15]2[C:14]([CH3:23])([CH3:22])[CH2:13][CH2:12][C:11]([CH3:24])([CH3:25])[C:10]=2[CH:9]=1)\[CH3:6])/[CH:3]=[O:4]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22226108HCID 22226108, compound2×

Product 1

HCID 23510817(E)-2-Fluoro-3-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enalYield 89%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

A mixture of (E)-2-fluoro-3-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-en-1-ol (Intermediate 7, 1.01 g, 3.04 mmol), NMO (0.89 g, 7.60 mmol), TPAP (catalytic amount), and 4 Å molecular sieves (200 mg) in CH2Cl2—CH3CN (40 mL, 8 mL) was stirred at ambient temperature for 45 min. The mixture was loaded onto a pad of silica gel and eluted with 10% EtOAc-hexane to give the tide compound as a pale yellow solid (890 mg, 89%).

Workup

  1. washeluted with 10% EtOAc-hexane

Sources & evidence

ORD record
ord-5095336ba4514322b187fb443f5c2aca
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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