2-Oxazolidinone, 4-phenyl-, (4S)- → (4S)-4-Phenyl-3-(3-phenylprop-2-enoyl)-1,3-oxazolidin-2-one

HRID 1182164

반응식

HRID 1182164 반응식
[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:18](Cl)(=[O:27])/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[C:18](=[O:27])/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 7304242-Oxazolidinone, 4-phenyl-, (4S)-HCID 5354261Cinnamoyl ChlorideHCID 178418339Butyllithium

생성물 1

HCID 679769(4S)-4-Phenyl-3-(3-phenylprop-2-enoyl)-1,3-oxazolidin-2-one수율 97.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To (S)-(+)-4-phenyl-2-oxazolidinone (9.88 g, 60 mmol) in THF (150 mL) at −78° C., was added n-butyl lithium (37.7 mL, 1.6M in hexanes, 60 mmol) over a period of 30 minutes. THF (50 mL) was added to the resultant thick suspension and the reaction mixture allowed to warm up to facilitate stirring. Trans-cinnamoylchloride (11.5 g, 69 mmol) in THF (30 mL) was added dropwise. The reaction was stirred at room temperature overnight. The reaction mixture was quenched with a saturated ammonium chloride solution (50 mL) and stirred for 0.5h. The solvent was removed in vacuo, the residue dissolved in ethyl acetate, washed with water (300 mL), 5% sodium bicarbonate (200 mL) and brine (100 mL) and dried over sodium sulfate. The solvent was removed in vacuo to give a pale yellow solid. The compound was crystallized from ethylacetate and washed with hexanes to give 17.12 g (97%) of (S)-4-phenyl-3-[(E)-(3-phenyl-acryloyl)]-oxazolidin-2-one.

후처리

  1. temperatureto warm up
  2. stirringThe reaction was stirred at room temperature overnight
  3. customThe reaction mixture was quenched with a saturated ammonium chloride solution (50 mL)
  4. stirringstirred for 0.5h
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue dissolved in ethyl acetate
  7. washwashed with water (300 mL), 5% sodium bicarbonate (200 mL) and brine (100 mL)
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed in vacuo
  10. customto give a pale yellow solid
  11. customThe compound was crystallized from ethylacetate
  12. washwashed with hexanes

출처 및 근거

ORD 기록
ord-ff76ea94b6ee46ff9e350968efa3243f
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288548B2

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