Hexane → HCID 67905614, compound

HRID 654584Notes

Reaction equation

HRID 654584 reaction equation
[C:1]1([CH2:7][C@H:8]2[CH2:12][O:11][C:10](=[O:13])[NH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[C:19](Cl)(=[O:22])[CH2:20][CH3:21].CCCCCC>C1COCC1>[O:22]=[C:19]([N:9]1[C@@H:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][O:11][C:10]1=[O:13])[CH2:20][CH3:21].[O:11]1[CH2:12][CH2:8][NH:9][C:10]1=[O:13]

Participants

6

Reactant 4

HCID 8058HexaneHCID 62324Propionyl chlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 67905614HCID 67905614, compoundYield 131.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (S)-4-(Phenylmethyl)-2-oxazolidinone (17.5 g, 0.1 mole) in THF (250 ml) at -70° C. under a blanket of nitrogen was added 2.5M n-BuLi (0.11 mole, 44 ml) dropwise in 10 minutes. After 5 minutes, the clear cloudy solution was treated rapidly with propionyl chloride (10 g, 0.105 mole). The colorless solution was then slowly warmed to room temperature in the course of 1 hour, quenched with saturated ammonium chloride (20 ml) and diluted with ether (100 ml). The organic extract washed with water (20 ml), aqueous NaHCO3 (20 ml), dried over anhydrous MgSO4 and evaporated to give a viscous solid mass. Trituration with hexane (100 ml) gave the oxazolidinone 3-(1-OxoPropyl)-(S) -4-(Phenylmethyl)-2-Oxazolidinone (21 g, 90%) as white plates MP.44°-46° C.IR:3030, 2980, 1780, 1705, 1455 cm-1.

Workup

  1. customquenched with saturated ammonium chloride (20 ml)
  2. additiondiluted with ether (100 ml)
  3. extractionThe organic extract
  4. washwashed with water (20 ml), aqueous NaHCO3 (20 ml)
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated
  7. customto give a viscous solid mass

Sources & evidence

ORD record
ord-1606f4d036f54bd6b1b8f2c12dd9d688
Source dataset
uspto-grants-1992_07
Patent number
US05132457

Reaction notes

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