tert-Butyl methyl ether → [3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl]acetaldehyde

HRID 253357Notes

Reaction equation

HRID 253357 reaction equation
C(O[CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([O:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])[CH2:6]1)C=C.I([O-])(=O)(=O)=O.[Na+].[C:32]([O:36]C)(C)(C)[CH3:33]>C(OCC)C.O.[Os](=O)(=O)(=O)=O>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:15]2[O:16][C:17]([CH3:18])=[C:13]([CH2:12][O:11][CH:7]3[CH2:8][CH2:9][CH2:10][CH:5]([CH2:33][CH:32]=[O:36])[CH2:6]3)[N:14]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 23667635Sodium periodateHCID 587633724-(3-Allyloxycyclohexyloxymethyl)-2-(4-fluorophenyl)-5-methyloxazole

Product 1

HCID 86594696[3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl]acetaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

2.0 g of 4-(3-allyloxycyclohexyloxymethyl)-2-(4-fluorophenyl)-5-methyloxazole are dissolved in 50 ml of diethyl ether, and 3.8 g of sodium periodate, dissolved in 50 ml of water, are added. At 0° C., 1 ml of an osmium tetroxide solution (2.5% by weight in tert-butanol) is added, and the mixture is stirred vigorously at room temperature. After 8 h, 100 ml of methyl tert-butyl ether are added and the mixture is washed with a saturated sodium thiosulfate solution. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is purified on silica gel (n-heptane:ethyl acetate=1:1→1:5). This gives 1.4 g of [3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl]-acetaldehyde as a yellow-brown oil. C20H25NO4 (343.42), MS (ESI): 344 (M+H+), Rf (n-heptane:ethyl acetate=1:1)=0.25.

Workup

  1. additionare added
  2. washthe mixture is washed with a saturated sodium thiosulfate solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customThe residue is purified on silica gel (n-heptane:ethyl acetate=1:1→1:5)

Sources & evidence

ORD record
ord-5acb7c2469424b8796dd5609621eb3f3
Source dataset
uspto-grants-2011_01
Patent number
US07872034B2

Reaction notes

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