Hydrochloric Acid → HCID 10491506, compound

HRID 1707876Notes

Reaction equation

HRID 1707876 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]C.C([Li])CCC.[C:12]1([CH2:18][C@H:19]2[CH2:23][O:22][C:21](=[O:24])[NH:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.C1C[O:29]CC1>O>[O:29]=[C:5]([N:20]1[C@@H:19]([CH2:18][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:23][O:22][C:21]1=[O:24])[CH2:4][CH2:3][CH:2]=[CH2:1]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8058HexaneHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 10491506HCID 10491506, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Another solution was prepared by adding dropwise a 1.6M hexane solution of butyllithium (38.8 mL, 62.1 mmol) to a cooled (-78°) solution of (S)-4-(phenylmethyl)-2-oxazolidinone [10.0 g, 56.4 mmol, described by L. N. Predgen et al., J. Org. Chem., 54, 3231 (1989)] in THF (250 mL). The freshly prepared second solution was kept at -78° for 30 min and then quickly added via a cannula to the solution of mixed anhydride at -78°. The reaction mixture was stirred at -78° for 3 h. Thereafter, H2O (100 mL) and 10% aqueous HCl (50 mL) were added. The resulting mixture was extracted with EtOAc (2×250 mL). The combined extract was washed with a saturated aqueous solution of NaHCO3 and with brine, dried (Na2SO4) and concentrated under reduced pressure. Purification of the residue by flash chromatography (SiO2, eluent: hexane-EtOAc, 15:1) gave (4S)-3-(1-oxo-4-pentenyl)-4-(phenylmethyl)-2-oxazolidinone (10.85 g, 74%) as a colorless oil, 1H NMR (CDCl3) δ 7.34-7.2 (m,5H), 6.0-5.8 (m,1H), 5.16-5.0 (m,2H), 4.7 (m,1H), 4.2 (m,2H), 3.3 (dd,J=3.1 Hz,13.2 Hz,1H), 3.1-3.0 (m,2H), 2.75 (dd,J=9.6 Hz,13.3 Hz,1H), 2.5 (m,2H), mass spectrum: 260 (M+H)+.

Workup

  1. customAnother solution was prepared
  2. extractionThe resulting mixture was extracted with EtOAc (2×250 mL)
  3. extractionThe combined extract
  4. washwas washed with a saturated aqueous solution of NaHCO3 and with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by flash chromatography (SiO2, eluent: hexane-EtOAc, 15:1)

Sources & evidence

ORD record
ord-55baa13f59784adc9896f63ffcca99b5
Source dataset
uspto-grants-1994_10
Patent number
US05354767

Reaction notes

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