tert-Butyl methyl ether → {cis-3-[2-(3-Methoxyphenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl}-acetaldehyde

HRID 854666Notes

Reaction equation

HRID 854666 reaction equation
[CH2:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([O:10][CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[O:15][C:16]=2[CH3:17])[CH2:5]1)[CH:2]=C.I([O-])(=O)(=O)=[O:27].[Na+].C(OC)(C)(C)C>C(OCC)C.O.[Os](=O)(=O)(=O)=O>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([C:14]2[O:15][C:16]([CH3:17])=[C:12]([CH2:11][O:10][C@@H:6]3[CH2:7][CH2:8][CH2:9][C@H:4]([CH2:1][CH:2]=[O:27])[CH2:5]3)[N:13]=2)[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 23667635Sodium periodateHCID 692437494-(cis-3-Allylcyclohexyloxymethyl)-2-(3-methoxyphenyl)-5-methyloxazole

Product 1

HCID 86597948{cis-3-[2-(3-Methoxyphenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl}-acetaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

750 mg of 4-(cis-3-allylcyclohexyloxymethyl)-2-(3-methoxyphenyl)-5-methyloxazole are dissolved in 20 ml of diethyl ether, and 1.4 g of sodium periodate, dissolved in 20 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 hours, 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 MgSO4 and the solvent is then removed under reduced pressure. This gives 740 mg of {cis-3-[2-(3-methoxyphenyl)-5-methyloxazol-4-ylmethoxy]-cyclohexyl}acetaldehyde as a yellow-brown oil. C20H25NO4 (343.43), MS(ESI): 344 (M+H+), Rf(n-heptane:ethyl acetate=2:1)=0.10.

Workup

  1. additionare added
  2. washthe mixture is washed with a saturated sodium thiosulfate solution
  3. dry with materialThe organic phase is dried over MgSO4
  4. customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-900ce8226e8640798b320eaceb771fff
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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