Potassium Hydroxide → HCID 9994621, compound

HRID 728249Notes

Reaction equation

HRID 728249 reaction equation
[CH2:1]([CH:8]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C:9]([O:11]C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO.O>[CH2:1]([CH:8]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10403037HCID 10403037, compound

Product 1

HCID 9994621HCID 9994621, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The methyl 2-benzyl-3-(t-butyldimethylsilyloxy)propionate (3.3 g) was dissolved in 100 ml of methanol, cooled to 0° C. and treated with 50 ml of 30% potassium hydroxide with vigorous stirring. The reaction was then allowed to warm to room temperature over five hours. The reaction was diluted with 200 ml of water, rinsed with diethyl ether, and the aqueous solution was cooled to 0° C. Dichloromethane (100 ml) was added, followed by the slow addition of 260 ml of 1M hydrochloric acid, with stirring. The layers were separated and the aqueous layer was extracted with dichloromethane (3×200 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was purified by radial chromatography (2% to 4% methyl alcohol in chloroform. 4 mm plate) to yield 2.14 9 of the 2-benzyl-3-(t-butyldimethylsilyloxy)propionic acid.

Workup

  1. temperatureto warm to room temperature over five hours
  2. washrinsed with diethyl ether
  3. temperaturethe aqueous solution was cooled to 0° C
  4. additionDichloromethane (100 ml) was added
  5. additionfollowed by the slow addition of 260 ml of 1M hydrochloric acid
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with dichloromethane (3×200 ml)
  8. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe residue was purified by radial chromatography (2% to 4% methyl alcohol in chloroform. 4 mm plate)

Sources & evidence

ORD record
ord-77cce52997ee4ed79b44cff6aee7f730
Source dataset
uspto-grants-1991_09
Patent number
US05047534

Reaction notes

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