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

HRID 849374ノート

反応式

HRID 849374 の反応式
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]

参加物

6

反応物 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 691051,3-Diethyl 2-oxopropanedioateHCID 53823235HCID 53823235、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c7064d795374b7cb05f088a0bb8de80
出典データセット
uspto-grants-2000_01
特許番号
US06011174

反応ノート

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