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

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.

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

ORDレコード

ord-ff76ea94b6ee46ff9e350968efa3243f

出典データセット

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07288548B2