Water → HCID 59541078, compound

HRID 1677468Notes

Reaction equation

HRID 1677468 reaction equation
[CH3:1][C:2]([CH3:17])([CH2:5][O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])[CH2:3][OH:4].C(Cl)(Cl)(Cl)Cl.O.I([O-])(=O)(=O)=[O:25].[Na+]>C(#N)C.CCOC(C)=O>[CH3:17][C:2]([CH3:1])([CH2:5][O:6][Si:7]([CH:8]([CH3:10])[CH3:9])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])[C:3]([OH:25])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 23667635Sodium periodateHCID 59540959HCID 59540959, compound

Product 1

HCID 59541078HCID 59541078, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,2-Dimethyl-3-triisopropylsilanyloxy-propan-1-ol (1.39 g, 5.34 mmol) (Journal of the American Chemical Society, 123(39), 9687-9688; 2001) dissolved in ACN (14 ml), CCl4 (14 ml), and water (22 ml) was treated with sodium periodate (4.57 g, 21.4 mmol) and then RuCl3—H2O (33 mg, 0.16 mmol). After stirring at room temperature for approximately 2 hours, the reaction mixture was partitioned between DCM/water. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a black oil. Silica gel chromatography using 0-30% EtOAc in hexanes as eluant provided 1.23 mg (84%) of 2,2-dimethyl-3-triisopropylsilanyloxy-propionic acid. M−H=569.

Workup

  1. customthe reaction mixture was partitioned between DCM/water
  2. customThe organic layers were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customgiving a black oil

Sources & evidence

ORD record
ord-76a5765809d84b5a87aede651da5fc1a
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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