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

HRID 849374노트

반응식

HRID 849374 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1c7064d795374b7cb05f088a0bb8de80
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011174

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