2-(2-Bromoethoxy)tetrahydro-2H-pyran → HCID 57704533, compound

HRID 2406034Notes

Reaction equation

HRID 2406034 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].Br[CH2:27][CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1>O1CCCC1.[Cl-].[Na+].O>[CH2:18]([O:17][C:15](=[O:16])[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])([CH2:27][CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:19]

Participants

6

Reactant 3

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 382219Diethyl 2-((tert-butoxycarbonyl)amino)malonateHCID 23676156Sodium t-butoxide

Product 1

HCID 57704533HCID 57704533, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Diethyl (t-butyloxycarbonyl)aminomalonate (52.3 g) was dissolved in tetrahydrofuran (400 ml), sodium t-butoxide (19.2 g) was added thereto, a solution of 2-(2-bromoethoxy)tetrahydro-2H-pyran (40.4 g) in tetrahydrofuran (100 ml) was added to the reaction mixture at 70° C., and the mixture was stirred with heating for 10 hr. After cooling, the reaction mixture was poured into saturated brine. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give the object product (50.0 g) as a colorless oil.

Workup

  1. temperaturewith heating for 10 hr
  2. temperatureAfter cooling
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c26ce8837e6c43d58d362cc3fd15f8ba
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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