Hexane → 4-tert-butyl 2,2-diethyl (4S)-1,3-dioxolane-2,2,4-tricarboxylate

HRID 849374Notes

Reaction equation

HRID 849374 reaction equation
Br[C@H:2]([CH2:10][OH:11])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[O:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15].CCCCCC.C(=O)([O-])[O-].[K+].[K+]>O>[O:11]1[CH2:10][C@@H:2]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[O:12][C:13]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 691051,3-Diethyl 2-oxopropanedioateHCID 53823235HCID 53823235, compound

Product 1

HCID 867550364-tert-butyl 2,2-diethyl (4S)-1,3-dioxolane-2,2,4-tricarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.90 g of tert-butyl (2R)-2-bromo-3-hydroxypropionate and 5.3 g of diethyl ketomalonate were mixed, and after the heat-generated reaction solution returned to room temperature, 15 ml of hexane and 6.4 g of potassium carbonate were sequentially added, followed by stirring at room temperature for 15 hours. Water was added to the reaction solution, followed by extraction with ethyl ether. The obtained organic layer was washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1) to obtain 8.0 g (yield: 83%) of the above identified compound as a colorless oily substance.

Workup

  1. customreturned to room temperature
  2. extractionfollowed by extraction with ethyl ether
  3. washThe obtained organic layer was washed with water
  4. dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1)
  8. customto obtain 8.0 g (yield: 83%) of the

Sources & evidence

ORD record
ord-1c7064d795374b7cb05f088a0bb8de80
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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