4-Pentenoyl chloride → HCID 68468485, compound

HRID 2235251Notes

Reaction equation

HRID 2235251 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[C:24](Cl)(=[O:29])[CH2:25][CH2:26][CH:27]=[CH2:28]>C1COCC1>[C:24]([N:8]1[C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@@H:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:10][C:9]1=[O:18])(=[O:29])[CH2:25][CH2:26][CH:27]=[CH2:28]

Participants

5

Reactant 3

HCID 42284934-Pentenoyl chlorideHCID 9859564(4S,5R)-(-)-cis-4,5-Diphenyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 68468485HCID 68468485, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Charge a 250 mL, single-neck, round-bottomed flask with (4S,5R)-4,5-diphenyloxazolidin-2-one (5.0 g, 21.0 mmol) and THF (300 mL). Stir the mixture at −78° C. and add dropwise BuLi (13.7 mL, 21.9 mmol). Stir the reaction mixture for 0.5 hours and then add pent-4-enoyl chloride (3.71 g, 31.3 mmol). Stir the reaction mixture one hour until TLC shows that the starting material has been consumed. Add water (100 mL) and extract the aqueous with CH2Cl2 (3×250 mL). Combine the organic layers and dry over Na2SO4. Concentrate and purify by chromatography (Silica gel) to afford (4S,5R)-3-Pent-4-enoyl-4,5-diphenyloxazolidin-2-one (4.49 g, 67%).

Workup

  1. stirringStir the reaction mixture for 0.5 hours
  2. stirringStir the reaction mixture one hour until TLC
  3. customhas been consumed
  4. extractionAdd water (100 mL) and extract the aqueous with CH2Cl2 (3×250 mL)
  5. dry with materialCombine the organic layers and dry over Na2SO4
  6. concentrationConcentrate
  7. custompurify by chromatography (Silica gel)

Sources & evidence

ORD record
ord-9982de5e49b84b3d92d44b33914427aa
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

Loading…