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

HRID 1883278Notes

Reaction equation

HRID 1883278 reaction equation
[F:1]/[C:2](=[C:5](/[C:8]1[C:17]([O:18][CH2:19][O: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][CH3:7])/[CH2:3][OH:4].C[N+]1([O-])CCOCC1>CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.C(Cl)Cl>[F:1]/[C:2](=[C:5](/[C:8]1[C:17]([O:18][CH2:19][O: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)\[CH2:6][CH3:7])/[CH:3]=[O:4]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 69729376(E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-en-1-ol2×

Product 1

HCID 60098606(E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enal

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Following General Procedure D and using (E)-2-fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-en-1-ol (Intermediate 16, 1.69 g, 4.83 mmol), NMO (1.4 g, 12.1 mmol), TPAP (catalytic amount), and CH2Cl2 (5 mL) followed by flash column chromatography on silica gel (5% EtOAc-hexane) the title compound was obtained as a off-white solid (1.48 g, 88%).

Sources & evidence

ORD record
ord-5696eec8d1a24330b8e8a6b0d024990c
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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