Hexane → (2E)-2-Fluoro-3-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-but-2-enal

HRID 2180512Notes

Reaction equation

HRID 2180512 reaction equation
[F:1]/[C:2](=[C:5](/[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[O:13][C:12]([CH3:20])([CH3:19])[CH:11]=[C:10]2[CH:21]([CH3:23])[CH3:22])\[CH3:6])/[CH2:3][OH:4].C[N+]1([O-])CCOCC1.CCCCCC.C(OCC)(=O)C>ClCCl.C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1]/[C:2](=[C:5](/[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[O:13][C:12]([CH3:20])([CH3:19])[CH:11]=[C:10]2[CH:21]([CH3:23])[CH3:22])\[CH3:6])/[CH:3]=[O:4]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 22490960(2E)-2-Fluoro-3-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-but-2-en-1-ol2×

Product 1

HCID 22490793(2E)-2-Fluoro-3-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-but-2-enal

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 21877088Acetonitrile methylene chlorideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (2E)-2-fluoro-3-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-but-2-en-1-ol (Compound 82, 117 mg, 0.37 mmol) in dichloromethane/acetonitrile (6:1, 7 mL) at 25° C. were added 4-methylmorpholine N-oxide (85 mg, 0.74 mmol), tetrapropylammonium perruthenate (12 mg, 0.04 mmol), and 4 Å molecular sieve powder (60 mg). The mixture was stirred at 25° C. for 1 h and applied directly to chromatography. Flash chromatography (silica gel, 100% hexane to 5% ethyl acetate in hexanes) gave rise to the title compound as a colorless oil.

Sources & evidence

ORD record
ord-6cd7463d24064351b23d1e045ec1d37c
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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