Hexane → HCID 22877217, 화합물

HRID 1379594

반응식

HRID 1379594 반응식
[CH3:1][CH:2]([C@@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[CH3:3].[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].[O:21]1CCNC1=O>C1COCC1>[CH3:1][CH:2]([C@@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:16](=[O:21])[CH2:17][C@@H:18]([CH3:19])[C:12]1[CH:11]=[CH:10][CH:15]=[CH:14][CH:13]=1)[CH3:3]

참가 물질

6

반응물 4

HCID 8058HexaneHCID 739492-OxazolidinoneHCID 641505(4R)-4-(Propan-2-yl)-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

생성물 1

HCID 22877217HCID 22877217, 화합물수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

In a separate preparation, a solution of 4(R)-(1-methylethyl)-2-oxazolidinone (3.06 g, 23.7 mmol) in dry THF (30 mL) was cooled to -50°. Under argon, a 1.6M hexane solution of butyllithium (14.8 mL, 23.7 mmol) was added dropwise to the cooled solution of the oxazolidinone derivative. After 15 min at -78°, a solution of the first reactant in dry THF (10 mL) was added. The reaction mixture was stirred at -70° for 30 minutes and then allowed to warm to room temperature over a 45 min period. The mixture was quenched with excess 10% aqueous NH4Cl. Thereafter, the THF was removed under reduced pressure and the resulting concentrate was dissolved in EtOAc. The solution was washed with 5% aqueous NaHCO3 (2 X) and brine (2 X), dried (MgSO4) and concentrated to give an oil. The oil was purified by flash chromatography [SiO 2, hexane-EtOAc (43:7)] to yield (4R)-(1-methylethyl)-3-(3(R)-methyl-1-oxo-3-phenylpropyl)- 2-oxazolidinone (6.1 g, 93% yield).

후처리

  1. customIn a separate preparation
  2. customThe mixture was quenched with excess 10% aqueous NH4Cl
  3. customThereafter, the THF was removed under reduced pressure
  4. concentrationthe resulting concentrate
  5. dissolutionwas dissolved in EtOAc
  6. washThe solution was washed with 5% aqueous NaHCO3 (2 X) and brine (2 X)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give an oil
  10. customThe oil was purified by flash chromatography [SiO 2, hexane-EtOAc (43:7)]

출처 및 근거

ORD 기록
ord-50c3be0e61a14d71bb6aaf33c311ad7a
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05672586

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