Sodium periodate → [cis-3-(Tert-butyl-diphenylsilanyloxy)cyclohexyl]acetaldehyde

HRID 347414Notes

Reaction equation

HRID 347414 reaction equation
[CH2:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:5]1)[CH:2]=C.I([O-])(=O)(=O)=[O:29].[Na+]>C(OCC)C.O.[Os](=O)(=O)(=O)=O>[Si:11]([O:10][C@@H:6]1[CH2:7][CH2:8][CH2:9][C@H:4]([CH2:1][CH:2]=[O:29])[CH2:5]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodate2×HCID 69242153(cis-3-Allylcyclohexyloxy)-tert-butyldiphenylsilane

Product 1

HCID 86594888[cis-3-(Tert-butyl-diphenylsilanyloxy)cyclohexyl]acetaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

5.5 g of (cis-3-allylcyclohexyloxy)-tert-butyl-diphenylsilane are dissolved in 100 ml of diethyl ether, and 9.4 g of sodium periodate, dissolved in 100 ml of water, are added. At 0° C., 15 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 5 hours, a further 5 g of sodium periodate are added, and the mixture is stirred at room temperature for another 3 hours. The reaction mixture is then diluted by addition of 300 ml of methyl tert-buthyl ether and washed with saturated sodium thiosulfate solution. The organic phase is dried over magnesium sulfate and the solvent is then removed under reduced pressure. This gives 6 g of [cis-3-(tert-butyl-diphenylsilanyloxy)cyclohexyl]acetaldehyde as a yellow-brown oil. C24H32O2Si (380.61), MS(ESI): 381 (M+H+), Rf(n-heptane:ethyl acetate=5:1)=0.44.

Workup

  1. additionare added
  2. stirringthe mixture is stirred at room temperature for another 3 hours
  3. additionThe reaction mixture is then diluted by addition of 300 ml of methyl tert-buthyl ether
  4. washwashed with 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-c51edd30202b4c52a9730302d3aba7d8
Source dataset
uspto-grants-2007_02
Patent number
US07173151B2

Reaction notes

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