Diethyl Ether → HCID 20624365, compound

HRID 2065859Notes

Reaction equation

HRID 2065859 reaction equation
CON(C)[C:4]([CH:6]1[CH2:10][S:9][C:8]([CH3:12])([CH3:11])[N:7]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:5].C(OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)[O-].[K+]>O>[CH:4]([CH:6]1[CH2:10][S:9][C:8]([CH3:12])([CH3:11])[N:7]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:5]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 59229153HCID 59229153, compound

Product 1

HCID 20624365HCID 20624365, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask containing tert-butyl 4-(methoxy(methyl)carbamoyl)-2,2-dimethylthiazolidine-3-carboxylate (2), 0.918 g, 3 mmol and diethyl ether (20 mL) was cooled in an ice bath. To the cooled solution, lithium aluminum hydride (160 mg, 4.2 mmol) was added. After 1 h additional ether (20 mL) was added. After an additional 1 h, a solution of potassium bisulfate (315 mg) in water (1 mL) was added carefully to the reaction. Celite was added, the mixture was filtered, and the solids were rinsed with additional ether. The collected ether was washed with 0.1 N HCl(aq) (15 mL), saturated sodium bicarbonate (15 mL), and brine (15 ml). The ether was dried over Na2SO4, evaporated and used without further purification. Yield 684 mg (92%)

Workup

  1. temperaturewas cooled in an ice bath
  2. additionCelite was added
  3. filtrationthe mixture was filtered
  4. washthe solids were rinsed with additional ether
  5. washThe collected ether was washed with 0.1 N HCl(aq) (15 mL), saturated sodium bicarbonate (15 mL), and brine (15 ml)
  6. dry with materialThe ether was dried over Na2SO4
  7. customevaporated
  8. customused without further purification

Sources & evidence

ORD record
ord-b033882683ea431993b67cc061017c0c
Source dataset
uspto-grants-2012_10
Patent number
US08288559B2

Reaction notes

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