tert-Butyl methyl ether → Tert-butyl 2-ethyl-4-[cis-3-(2-oxoethoxy)cyclohexyl]butyrate

HRID 347419Notes

Reaction equation

HRID 347419 reaction equation
[CH2:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([CH2:11][CH2:12][CH:13]([CH2:21][CH3:22])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6]1)[CH:2]=C.I([O-])(=O)(=O)=[O:24].[Na+].C(OC)(C)(C)C>C(OCC)C.O.[Os](=O)(=O)(=O)=O>[CH2:21]([CH:13]([CH2:12][CH2:11][C@H:7]1[CH2:8][CH2:9][CH2:10][C@@H:5]([O:4][CH2:1][CH:2]=[O:24])[CH2:6]1)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:22]

Participants

7

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 23667635Sodium periodateHCID 69494301Tert-butyl 4-(cis-3-allyloxycyclohexyl)-2-ethylbutyrate

Product 1

HCID 86594889Tert-butyl 2-ethyl-4-[cis-3-(2-oxoethoxy)cyclohexyl]butyrate

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalyst2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

770 mg of tert-butyl 4-(cis-3-allyloxycyclohexyl)-2-ethylbutyrate are dissolved in 50 ml of diethyl ether, and 1.59 g of sodium periodate, dissolved in 50 ml of water, are added. At 0° C., 2.56 ml of an osmium tetroxide solution (2.5% by weight in tert-butanol) are added, and the mixture is stirred vigorously at room temperature. After 9 hours, a further 12.8 ml of the osmium tetroxide solution are added, and stirring at room temperature is continued for a further 3 hours. 200 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 then removed under reduced pressure. This gives 710 mg of tert-butyl 2-ethyl-4-[cis-3-(2-oxoethoxy)cyclohexyl]butyrate as a yellow-brown oil. C18H32O4 (312.45), Rf(n-heptane:ethyl acetate=5:1)=0.15.

Workup

  1. additionare added
  2. stirringstirring at room temperature
  3. waitis continued for a further 3 hours
  4. washthe mixture is washed with a saturated sodium thiosulfate solution
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-a9913215dd1849fbb174baa77512dfb9
Source dataset
uspto-grants-2007_02
Patent number
US07173151B2

Reaction notes

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