Triethylamine → 3-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoyl]-oxazolidin-2-one

HRID 322070ノート

反応式

HRID 322070 の反応式
CCN([CH2:6][CH3:7])CC.[C:8](Cl)(=[O:13])[C:9](C)(C)[CH3:10].[O:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20].[Li]CCCC.[Li].[C:27]([O:30][CH2:31][CH3:32])(=[O:29])[CH3:28]>C1COCC1>[CH3:28][C:27]1([CH2:6][CH2:7][CH2:10][CH2:9][C:8]([N:17]2[CH2:18][CH2:19][O:15][C:16]2=[O:20])=[O:13])[O:29][CH2:32][CH2:31][O:30]1

参加物

8

反応物 6

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 62493Pivaloyl chlorideHCID 739492-OxazolidinoneHCID 3028194LithiumHCID 178418339Butyllithium

生成物 1

HCID 154537573-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoyl]-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred solution of 2-2 (16.0 g, 85.5 mmol), NEt3 (13.1 ml, 94.1 mmol) and THF (400 mL) at −78° C. was added pivaloyl chloride (11.6 ml, 94.1 mmol). The mixture was warmed to 0° C. for 1.0 h and then recooled to −78° C. To a stirred solution of 2-oxazolidinone (9.3 g, 106.9 mmol) and THF (200 ml) at −78° C. was added nBuLi (43.0 ml, 106.9 mmol, 2.5M in hexanes) dropwise over 10 minutes. After 20 minutes, the lithium reagent was transferred to the mixed anhydride via cannula. After 10 minutes, the reaction was warmed to 0° C. for 1.0 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 40%-50% EtOAc/hexanes) to give 2-3 as a colorless foam.

後処理

  1. customrecooled to −78° C
  2. waitAfter 10 minutes
  3. temperaturethe reaction was warmed to 0° C. for 1.0 h
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. customremoval of the solvent
  7. customthe residue was chromatographed (silica gel, 40%-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ba4689a5c6be4bc5ad66c4444783f98b
出典データセット
uspto-grants-2001_04
特許番号
US06211191B1

反応ノート

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