Potassium Sodium Tartrate → HCID 131729831, compound

HRID 1514665Notes

Reaction equation

HRID 1514665 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:8][O:9][C:10]=1[C:11]([CH3:19])([CH3:18])[O:12][SiH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O)C.[BH4-].[Li+].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[C:14]([SiH2:13][O:12][C:11]([CH3:19])([CH3:18])[C:10]1[O:9][N:8]=[C:7]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:6]=1[CH2:4][OH:3])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 4148881Lithium borohydrideHCID 131729832HCID 131729832, compound

Product 1

HCID 131729831HCID 131729831, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenyl-isoxazole-4-carboxylic acid ethyl ester (12.2 g, 34 mmol) was dissolved in THF (200 mL), lithium borohydride (1.47 g, 67 mmol) was added and the reaction mixture was heated under reflux overnight. After cooling to room temperature aqueous saturated Seignette salt solution was added and the mixture was stirred for 1 h. After extractive workup (ethyl acetate/diethylether) the organic phase was dried over sodium sulfate, filtered and concentrated. Chromatographic purification (silica, heptane:ethyl acetate=100:0 to 85:15) afforded the title compound as a light yellow oil (4.4 g, 41%). MS: m/e=320.4 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. additionwas added
  4. dry with materialAfter extractive workup (ethyl acetate/diethylether) the organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customChromatographic purification (silica, heptane:ethyl acetate=100:0 to 85:15)

Sources & evidence

ORD record
ord-f1d8b2db11d744cf846ed5e31d3f9e8e
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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