Water → Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-oxoethyl)cyclohexanone ethylene ketal

HRID 1650048Notes

Reaction equation

HRID 1650048 reaction equation
[CH2:1]1O[C:4]2([CH2:9][CH2:8][C@@H:7]([CH2:10][CH:11]=C)[C@H:6]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:27])([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:14]=3[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:5]2)[O:3][CH2:2]1.I([O-])(=O)(=O)=[O:38].[Na+].O1CCCC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:54]>[Os](=O)(=O)(=O)=O.CCOCC>[CH2:2]1[O:3][C:4]2([CH2:9][CH2:8][C@@H:7]([CH2:10][CH:11]=[O:38])[C@H:6]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:26])([CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:14]=3[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:5]2)[O:54][CH2:1]1

Participants

8

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 23667635Sodium periodateHCID 86738780Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone ethylene ketal

Product 1

HCID 86738782Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-oxoethyl)cyclohexanone ethylene ketalYield 59%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 17.0 g. (34.7 mmoles) of trans-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone ethylene ketal, 44.5 g. (0.208 mmole) of sodium metaperiodate and 176 mg. (0.69 mmole) of osmium tetroxide in 340 ml. tetrahydrofuran and 100 ml. of water was stirred at room temperature for 3.5 hours. The reaction mixture was then added to 1000 ml. 15% sodium sulfite-1000 ml. ether. The organic phase was separated, washed twice with 500 ml. of saturated sodium bicarbonate, dried over magnesium sulfate and evaporated (aspirator). The residue was purified by column chromatography on 400 g. of silica gel eluted with 33-75% ether-petroleum ether to yield 10.0 g. (59%) of the title compound as an oil.

Workup

  1. additionA mixture of 17.0 g
  2. additionThe reaction mixture was then added to 1000 ml
  3. customThe organic phase was separated
  4. washwashed twice with 500 ml
  5. dry with materialof saturated sodium bicarbonate, dried over magnesium sulfate
  6. customevaporated (aspirator)
  7. customThe residue was purified by column chromatography on 400 g
  8. washof silica gel eluted with 33-75% ether-petroleum ether
  9. customto yield 10.0 g

Sources & evidence

ORD record
ord-30e523b027464f0d88429f58537284d0
Source dataset
uspto-grants-1990_05
Patent number
US04921994

Reaction notes

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