Potassium Sodium Tartrate → HCID 57205641, compound

HRID 1069093Notes

Reaction equation

HRID 1069093 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Si:11]([O:18][C@H:19]([C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=1)[C:20](OC)=[O:21])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Si:11]([O:18][C@H:19]([C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=1)[CH:20]=[O:21])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 53637572HCID 53637572, compound

Product 1

HCID 57205641HCID 57205641, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisobutylaluminum hydride (56.5 mL, 1.5 M in toluene) was added dropwise over 1 h to a cooled (−78° C.) solution of methyl (R)-2-[tert-butyl(dimethyl)silyl]oxy-2-(3,5-dichlorophenyl)ethanoate (14.81 g) in toluene (150 mL) under nitrogen. The resulting colorless solution was stirred at this temperature for 1 h, before a saturated aqueous solution of Rochelle's salt (70 mL) was added dropwise. The resulting mixture was allowed to warm to room temperature, and was then diluted with ethyl acetate. The biphasic system was filtered through celite, rinsing with water and ethyl acetate . The filtrate was separated into its two layers, and the aqueous layer was extracted with ethyl acetate. The extract and the organic layer of the filtrate were combined, washed with saturated aqueous sodium chloride solution, dried (magnesium sulfate), and concentrated to afford (2R)-2-[tert-butyl(dimethyl)silyl]oxy-2-(3,5-dichlorophenyl)ethanal as a colorless oil (13.36 g). Based on its 1H-NMR spectrum, the title compound made up ca. 50% of the oil.

Workup

  1. additionwas added dropwise
  2. filtrationThe biphasic system was filtered through celite
  3. washrinsing with water and ethyl acetate
  4. customThe filtrate was separated into its two layers
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. extractionThe extract
  7. washwashed with saturated aqueous sodium chloride solution
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-11b6bde01e9544018c4107f8c276dcd8
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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