Hexanoyl chloride → HCID 10858719, compound

HRID 601715Notes

Reaction equation

HRID 601715 reaction equation
[CH3:1][C@@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[NH:3]1.[Li]CCCC.[C:19](Cl)(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[C:19]([N:3]1[C@H:2]([CH3:1])[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4]1=[O:13])(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 67340Hexanoyl chlorideHCID 2733812(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 10858719HCID 10858719, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4R,5S)-(+)-4-methyl-5-phenyl-2-oxazolidinone (Aldrich Chemicals, 1.77 g, 10 mmol) in THF (100 mL) at −78° C. was added nBuLi (6.6 mL, 1.6 M in Hexane, 10.6 mmol) dropwise. After 10 minutes, hexanoyl chloride (1.68 mL, 12 mmol) was added. After 30 minutes the solution was allowed to warm to rt, at which time the reaction was quenched with saturated ammonium chloride solution. After 10 minutes, 1 M NaOH was added, and the mixture extracted 3 times with ethyl acetate. The combined organic layers were dried with MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (0% to 20% EtOAc/Hexane gradient) afforded pure product (1.98 g, 72%). 1H NMR (500 MHz, CDCl3) δ ppm 0.96-0.81 (m, 6H) 1.40-1.26 (m, 4H) 1.74-1.59 (m, 2H) 3.04-2.81 (m, 2H) 4.75 (dt, J=13.8, 6.7 Hz, 1H) 5.64 (d, J=7.32 Hz, 1H) 7.44-7.23 (m, 5H).

Workup

  1. waitAfter 30 minutes the solution was allowed
  2. customwas quenched with saturated ammonium chloride solution
  3. waitAfter 10 minutes
  4. addition1 M NaOH was added
  5. extractionthe mixture extracted 3 times with ethyl acetate
  6. dry with materialThe combined organic layers were dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8441dfd3b063402a8267ad515e43af76
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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