Methyl morpholine oxide → 4-(5-(4-(2-(S)-Butoxy)-3-trifluoromethylphenyl)-1,2,4-oxadiazol-3-yl)benzaldehyde

HRID 1268928Notes

Reaction equation

HRID 1268928 reaction equation
[CH3:1][C@H:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=3)[N:13]=2)=[CH:8][C:7]=1[C:25]([F:28])([F:27])[F:26])[CH2:3][CH3:4].C[N+]1([O-])CCOCC1>CC#N.C([N+](CCC)(CCC)CCC)CC>[CH3:1][C@H:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][CH:18]=3)[N:13]=2)=[CH:8][C:7]=1[C:25]([F:28])([F:26])[F:27])[CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 184469714-(5-(4-(2-(S)-Butoxy)-3-trifluoromethylphenyl)-1,2,4-oxadiazol-3-yl)phenylmethanol

Product 1

HCID 184469704-(5-(4-(2-(S)-Butoxy)-3-trifluoromethylphenyl)-1,2,4-oxadiazol-3-yl)benzaldehydeYield 65%

Reagents, catalysts & solvents 2

HCID 9559TetrapropylammoniumCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 510 mg (1.3 mmol) of 4-(5-(4-(2-(S)-methylpropyloxy)-3-trifluoromethylphenyl)-1,2,4-oxadiazol-3-yl)phenylmethanol (from Step C), 153 mg (1.3 mmol) of 4-methylmorpholine N-oxide and 510 mg of 4 A molecular sieves in 8 mL of CH3CN was treated with 13 mg (0.04 mmol) of tetrapropylammonium perruthnate and the resulting mixture was stirred ar rt for 2 h. The solids were filtered and the filtrate was concentrated. Chromatography on a Biotage 40 S cartridge using 9:1 v/v hexanes/EtOAc (1 L) as the eluant afforded 330 mg of the title compound: 1H NMR (500 Mhz) δ 1.01 (t, J=7.3, 3H), 1.38 (d, J=5.9, 3H), 1.73–1.83 (m, 2H), 4.56 (sextet, 1H), 7.14 (d, J=8.9, 1H), 8.02 (d, J=8.2, 2H), 8.30 (d, J=8.2, 2H), 8.32 (d, J=8.9, 1H), 8.44 (s, 1H), 10.1 (s, 1H).

Workup

  1. filtrationThe solids were filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d790fde5e5304ba5b5e612adc6af5a7d
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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